Coriolin & Related Natural Products
Gallagher
Matsumoto, Tet. Lett., 1969, 3913
Triquinane Natural Products:
1) BrCH2C(O)Et
NaH
O
Me
DMF-PhH
2) 20% HClO4
MeO2C
Me
OH
O
H Me
O
Me
Me
OH
H Me
O
Me
O
H
1) excess NaH
PhH
O
Me 2) H2 Pd/C
Me
Me
O
Me
H
Me
O
H
H
OH
O
Nozoe, Tet. Lett., 1976,195 (identification and first synthesis of (±)–hirsutene).
coriolin
H
H
hypnophilin
Me
Tatsuda, J. Antibiotics, 1980, 33, 100.
Danishefsky, J. Am. Chem. Soc. 1980,102, 2097.
Ikegami, Tet. Lett. 1980, 21, 3587.
Trost, J. Am. Chem. Soc., 1981, 103, 7380.
Mehta, J. Chem. Soc. Chem. Commun.,1982, 540.
Wender,Tet. Lett., 1983, 24, 5325.
Demuth, J. Am. Chem. Soc., 1986, 108, 4149.
Wender, J. Am. Chem. Soc., 1987, 109,
Curran, J. Am. Chem. Soc., 1988, 110, 5064.
Paquette, J. Am. Chem. Soc., 2002, 124, 9199.
Paquette, J. Am. Chem. Soc., 2002, 124, 9199.
O
Me
H
Me
NaH, Allyl-Cl
DME, 71%
O
Me
CH2PPh3,
Me
Me
Me H
H
Me H
240 ˚C,
Ar(g),
83%
H
H
Me
Ag2O-NaOH
Me
Me
HO2C
H
Me
Me H
Me H
Me
1) OsO4,
2) NaIO4
50%
Me
Me H
O
(COCl)2, pyr.
H Me
Me
H Me
Me
Me
Me
Me
H
H
hirsutene
Nozoe, Tet. Lett., 1976,195.
Matsumoto, Tet. Lett., 1976, 2795
Tatsuda, J. Am. Chem. Soc., 1979, 101, 6116-8
Mehta, J. Chem. Soc. Chem. Commun.,1981, 756.
H
ceratopicanol
Cl
Me
SnCl4, CS2
Me
Me
Me OH
Cl(O)C
H
H
H
Me
Me H
O
+
H
20%
H
Paquette, J. Am. Chem. Soc., 2002, 124, 9199.
O
1) Li, NH3,
tBuOH
2) CrO3, pyr.
60%
H
Me
Me
Me
H
O
excess CH2PPh3
70%
O
Me
H
20%
H
H
Me
Me
Me
H
(±)–hirsutene
Coriolin & Related Natural Products
Matsumoto, Tet. Lett., 1975, 4377 (7-keto (13)-norprotoilludane).
Matsumoto, Tet. Lett., 1976, 2795 ((±)–hirustene)
Tatsuda, J. Am. Chem. Soc., 1979, 101, 6116-8 ((±)–hirsutene)
O
O
A proposed biogenesis of hirsuteneBiogenesis is thought to originate with cation initiation here.
H
H
Me
Me
H
H
H
Me
O
O
Me
hn
H
Me
H
Me
H
Me
Me
H Me
H
CH3PPh3Br
Me
tAmONa,
PhH, 92%
H
H
Me
Me
Me
7-keto (13)-norprotoilludane
Me 8%
Me
O
Me
NaBH4
H EtOH, 100%
H
H
H
Me
H
Me
Me
pTsOH
PhH
Me
OH
Me 40%
H
Me
OMOM
O Me
O
H
H
Me
pTsOH
PhH, 95%
Me
CH3PPh3Br,
PhH, 92%
H
Me
H Me
OTs
Me
OMOM
O Me
O
O
cat. H2SO4
acetone
87%
Me
OMOM
H Me
1) Pd/C, H2
Me
MeOH
2) LiAlH4
87%
Me
H
H
Me
Me
Me
OH
OMOM
H Me
Me
CH2
Me
Me
Me
H
H
MsCl
Me
Pyr., 70%,
7:1
endo
v.
exo
Me
H Me OH
elimination
H
O
H
Me
Me
H
O
H Me
H
Me
1) cat. H2SO4
2) PCC
Me
86%
H
OMOM
H Me
H
H
Tatsuda, J. Antibiotics, 1980, 33, 100 ((±)–coriolin).
O
H Me
H
H
1) NaH, CS2
imid., MeI, THF,
100%
2) Bu3SnH
90%
H
H
O
H OH
OH
(Nozoe intermediate to (±)–hirsutene)
LiAlH4
THF
Me
H OH
OTs
Me
H
O Me OMOM
O
TsCl, pyr.,
Me
82%
Me
O
mCPBA,
CH2Cl2,
98%
H
Me
tAmONa,
Me
H Me
O Me OMOM
O
H
Me
Me
Me
K2CO3
acetone
90%
30%
H2SO4, 95%
CrO3
H
H OAc
NaI, Zn
DMF(aq)
56%
H
OH
Me
NaOMe
74%
1%
H
H
Me
H OAc
OAc
H Me O
Me
O
Me
H
Me
O Me OMOM
O
Me
1) NaBH4
2) MOMCl Me
N(iPr)2Et
H OAc
OAc 35%
OAc +
O
Me
H
Me
H
O Me O
O
O
Me
Tl(ClO4)3
tBuOH-H O, 57%
2
Me
O
Me
Me
Me
75% H
+
Me
Me
H Me
H
Me
H
Me
Me
Me
H
Me
H
Me
Me
H
Me
1) Br2
O
O
2) (CH2OH)2,
Me
pTsOH
AcO
Me
3) tBuOK
hn
4) NBS, BzOOH
OAc
5) AcOAg
54%
Me
OH
H Me
O
Me
1) OsO4(cat), NMO Me
2) 2,2-DMP, pTsOH
H
85%
(72% from epoxide in
hirsutene synthesis)
OH
H Me
Me
H
O
O
Me
1) PCC, ~100%
2) NaH, methyl- Me
O 2-nitrophenyldisulfide
Me
Me
O
H Me
SMe
SMe
H
O
O
Me
Me
Coriolin & Related Natural Products
O
O
H Me
Me
O
SMe
Tl(NO3)3
SMe 54% from
alkoxy-ketal
Me
O
H
O
O
H Me
Me
Me
H
O
Li, NH3, 78%
(LAH is a worse choice:
product appears in a
1:7 epimeric ratio against
the desired configuration)
O
Me
HO Me
H OHH Me
OMe
Me
TFA
OMe
Me
OH
O
O
Me
Me
OH
H
OH
O
H Me
OAc
OH
Me
H Me
Me
O
H
Me
tBuOH
Me
Me
2) pTsOH
Benzene
70%
O
O
H
tBuOK,
tBuOH;
Me
H Me
Me
Li, NH3
MeOH
quant.
O
OH
DIBAL
85%
Me
H
H
O
LDA
O -30 ˚C – 0 ˚C;
PhSS(O)2Ph
40%
Me
OH
Me
H Me SPh
O
mCPBA
Me
Me
O
Me
OMe
H
H
OH
Me
OMe
H
Me
pTsOH, Tol.
Me 60-65%
OMe
Me
O
Me
Me
O
H
O
Me
Me
O
Me
HO Me
MeLi
THF
82%
Me 50% from endione
Me
O
Me
O
H
1) PhSeCl
Me 2) mCPBA
O
OH
O
H Me
O
H2O2, NaOH
Me
O
Me
Me
Me
TMSO
O
Me
OH
H Me
O
Me
Me
H
O
120 ˚C
Xylenes
TMSO
H
Me
O
OH
(±)-coriolin
(7:5 versus epi-spiro-coriolin)
Me
Me
OH
EtOAc,
∆
Me
MeO
O
O
OH
Me
H Me SPh
O
Me
OH
O
NaOMe,
MeOH
O
Me
O
MeO2C
Me
Me
H Me
Me
H
Danishefsky, J. Am. Chem. Soc. 1980,102, 2097 ((±)–coriolin)
+
O
Me
(±)–coriolin
MeO2C
Me
H Me
Me
1) mCPBA,
CH2Cl2
2) PCC
Me
H
1) tBuOAl
Me
Me
Me
Me
O
Me
O
O
Me
O
O
OH
Me
H Me
Me
1) 1N LiOH
Me
O 2) H2O2, NaHCO3
6% from epoxide
H
1) O3
2) H2SO4,
CrO3
3) BaOH
4) Pb(OAc)4
PhH
58% overall
H+
70%
MsCl,
DMAP
46%
H OAc
H Me
Me
O
HO Me
OMe
H
Me
Me
Me
Me
OH
Me
Me
HO Me
H OHH Me
OMe
OH
H
OAC
Me
H
O
H
Me
Me
Ac2O, pyr.
68%
HO Me
H Me
OMe
OMe
O
Me
HO Me
H OAc
H Me
H
Me
MeLi
OMe Et2O, 60% Me
Me
Me
O
OMe
H
OH
Coriolin & Related Natural Products
Ikegami, Chem. Lett., 1979, 1299.
Mehta, J. Chem. Soc. Chem. Commun., 1981, 756-7 ((±)–hirsutene).
Mehta, J. Chem. Soc. Chem. Commun., 1982, 540-1 ((±)–coriolin).
H
TMSO
O
35% yield
Ikegami, Tet. Lett. 1980, 21, 3587 ((±)–coriolin)
H
O
Me
H
Me2LiCu
Et2O, 95%
TMSO
tBuOK,
H
Me
O
Me
H
H
∆, 100%
1) Pd/C, H2 H
H
H
H
EtOAc,
∆
∆
Me 100%
Me
Me
2) tBuOK,
Me
Me H
Me H
Me H
O
MeI,
O
O
O
O
O
O
THF, 50%
14
:
49
:
37
1) NaBH4
(Equilibrium ratio following thermal activation)
2) MOMCl,
Hünig's Base
H
DHP, H+
Me ~100%
HO
H
Me
H
Me
OTHP
Me
TMSO
H
Me
O
Me
H
OTHP
H
NaH, DME;
O
Allyl-Br, 81%
(94% b.r.s.m.)
1) LiAlH4
H
H
THF
Me
Me
100%
2) NaH, CS2
Me
Me
Me H
Me H
imid., MeI,
MOMO
O
MOMO
OCS Me
THF, 100% (Tatsuta intermediate to 2(±)–hirsutene)
H
Me
Me
H
PdCl2, CuCl,O2,
DMF-H2O
Me
77%
OTHP
Me
H
H
H
H
O
Me
Me
O
H
OTHP
O
83%
HO
H Me
Me
H
THPO
1) PhSeBr;
H Me
Me
H
O
,
AcOH,
2 2
O
2) AcOH
Me
THF–H2O,
H
50%
O
LDA, MeI,
THF, 90% Me
H Me
O
Me
H
2:1 ratio of unconjugated
and conjugated products
mCPBA
CH2Cl2
HO
Me
H Me
Me
H
H
DBU, PhH
Me
O 21% (60% b.r.s.m.)
HO
1) LDA,
PhSeBr
2) H2O2,
THF,AcOH
35%
H Me
O
Me H
Me
OH
H
Me
O
Me H
H
OH
OH
Me
(Tatsuta intermediate to (±)–coriolin)
(Danishefsky/ Tatsuta
intermediate to (±)–coriolin)
H
H
Li, NH3,
MeOH, 63%
Me
Me
Me H
Me
OH
1) mCPBA,
Na2CO3
100%
2) BF3-Et2O
0-5 ˚C, 80%
H
O
O
Me
H
O
O
DME;
AcOH
HO
Me H
THPO
H Me
Me
tBuOk,
Me
1) NaH, MeI
H
THF, 65% H
2) MeMgI;
Me
NH4Cl
Me
Et2O, 90%
Me
Me H
3) POCl3-pyr. Me
O
75%
tBuOK,
tBuOH
Me
H
OH
5:2 miture of epimers;
desired carried forward,
undesired oxidized and
recycled
H
Me
Me
Me
OTHP
PCC, NaOAc
90%
O
O
O
Me
KF
TMSO
Me THF, ~100%
Me
Me
O
H
Me
hn
85%
Me
Li, NH3,
trace THF
H
O
O
Me
MeI
TMSO
THF, 77%
-78 ˚C – 0 ˚C
TMSO
O
Me
H
Me
∆
Me
"high yield"
+
H
Me 1) LDA, TMSCl
2) Pd(OAc)2, MeCN O
>90%
Me
H
Me
Me
Me H
Me
OH
Me
Coriolin & Related Natural Products
Trost & Curran, J. Am. Chem. Soc., 1981, 103, 7380 ((±)–coriolin).
"
" , J. Am. Chem. Soc., 1980, 102, 5699 (enedione).
O
Me
O + AcO
O
OEt
O
Me
Pd(PPh3)4, DBU
PhCH3, 76%
NBS, H2O, DMSO
89% crude
OEt
O
Me
Me
O
OH
H Me
Me
Br
O
1) (O,N-bis-(trimethylsilyl)trifluoroacetamide,
DMF
OTMS
2) LDA,
H Me
Me
THF-HMPA;
O
O Pyr. HF,
TMSCl
Me
85%
3) Me2N=CH2I
4) CH3I
H
5) DBU, 46% overall
OTMS
H
OH
K2CO3(aq)
75%
O
O
O
Me
Me
O
Me
O
PPh3
O
1) MeSH, NEt3(cat)
quant.
2) (CH2OH)2, CSA(cat)
70%, (92% b.r.s.m.)
O
O
Me
O
PPh3
O
KH, CH3SSCH3
DME, 72%
Br
+Br-
O
3) Ac2O, DMAP
79% overall
Me
Ms
TBAF
87%
PDC, 74%
Me
H
OH
O Me
O
O
Ms
H
Me
Me
H
H
(Danishefsky intermediate
to (±)–coriolin)
O
SMe
1) SOCl2, pyr.
Me
2) mCPBA
3) HClO4
Me
4) DBU
73% overall
O
1) mCPBA
2) DBU
63% overall
H
Me
H
Me
Li, NH3; pH 5.8
1
O
CO2Me
3 Steps
52%
64%
MOMO
2. MOMCl, KH
77%
hn
OH
H Me
Me
O
Me
+
MOMO
H
1. 9-BBN; H2O2,
NaOH 74%
2. PDC 80%
:
OH
1. Li
CHO
O Me
Na Napthalenide
DME -45 ˚C, 52%
OH
H Me
Me
O
H
O
TMS
Me
Ms
Me
Li, NH3
O
Et2O, EtOH Me
92%
Wender,J. Am. Chem. Soc, 1987, 24, 5325 ((±)–coriolin).
Ms
OH
H Me
Me
Me
Me
Me
mCPBA, NaHCO3 MeS
63%
Ms
Ms
O
Ms
O
OH
H
Me
TMS 72%
O
Me
O
Et2Zn, CH2I2,
PhCH3, O2(cat)
82%
PtO2, H2,
HO Me
O
HOAc, NaOAc,
94%
H
SMe
Ms
TMS
Me
Me
O
SMe
O
O
OH
Me
MeS
O
KH, DME
O
H
(Danishefsky intermediate
to (±)–coriolin)
1) hn
2) LiAlH4,
Et2O
23%
AcO
O
I
HO Me
O
Me
HO
O
Me
OH
H Me
Wender,Tet. Lett., 1983, 24, 5325 ((±)–coriolin).
1) Mg, Et2O
2)
O
O
Me
Me
O
Me
4
H
O
MOMO
MOMO
H
200 °C, 12 h
60%, 2 steps
H
Coriolin & Related Natural Products
MOMO
Curran, J. Am. Chem. Soc., 1988, 110, 5064 ((±)–coriolin)
MOMO
H
BF3•Et2O
66%
H
H
1.TBSO
O
OAc
OH
H
O
MOMO
1. B2H6, THF;
H2O2, NaOH
79%
2. PDC 90%
H
OH
H
5 steps
O
TBSO
Li, CuBr
O
62%
1. MsCl, Et3N 80%
2. 6N HCl/THF/H2O
66%
OH
Br
OH
2. LAH
90%, 2 steps
1. PCC
2. Li
TMS
98%
H
O
TMS
HO
H
85%
O
Me
Demuth, J. Am. Chem. Soc., 1986, 108, 4149 ((–)-coriolin).
O
O
(R,R)–DET, pTsOH
PhCH3, >96%
O
O
O
(rac)
O
1) Column, 34%
CO2Me 2) 1N HCl, EtOH
60˚C, 91%
O
Me
hn,
70-74%
2. pTsOH,
acetone
60%
O
H
LDA; TBSCl
THF/DMPU
89%
Me
Me
hn,
70-74%
OH
H
1. SmI2
THF/HMPA
hn,
70-74%
OH
H
O
O
DDQ
H
H Me
O
Cl
O
Me
, KBr,
tBuOK, tBuOH,
PhCH3, 95%
O
O
Me
H
Me
O +
Me
O
H
H
1) Li, NH3,
THF, tBuOH
2) OsO4, NaIO4
dioxane-H2O
43% over two steps
OH
H Me
Me
H
O
Me
H Me
Me
+ Me
O
Me
H
Me
H
Me
Me
t
t
O 1) BuOK, BuOH
Me
PhCH3
2) Oxone, pTsOH
isopropenylacetate
H
(Inert Side Product)
OH
H Me
O
H
OH
(Enantiopure analogue to Trost
intermediate to (±)–coriolin)
OH
H
2,6-lutidine
72%
(Danishefsky/ Tatsuta intermediate to (±)–coriolin)
Me
OH
O
(–)
CO2Me
O
O
+
O
O
Me Me
NaH, MeI
DME, r.t.;
NaH, MeI,
O 46%
O
PCC
(Ikegami intermediate
to (±)–coriolin)
TBSO
1. PCC
2. (CH2OH)2, H+
3. Bu4NF
53%, 3 steps
H
OTBS
Coriolin & Related Natural Products
Paquette, J. Am. Chem. Soc., 2002, 124, 9199 (hypnophilin, coriolin, ceratopicanol).
Me
iPrO
O
iPrO
O
O
H
O
Li
iPrO
H
H
Me
iPrO
O
H H
Me
OH
iPrO
iPrO
Me
OH
H
O
iPrO
OH
Me
OH H
H
O
H
Me
iPrO
iPrO
Me
H H
OH
O
Li, NH3
THF;
Li benzoate
72%
H
LDA, HMPA
Me THF, CH I
3
O
Me
iPrO
iPrO
Me
OMe
Br
tBuLi,
THF, -78 ˚C Me
Me
Me
O
Li
OMe
Me
1) AlH3
Br
2) MeI
Me
1) Ethylene glycol
O
Dowex 50X4-400, Me
Br
PhH, 80% b.r.s.m.
Me
2) tBuLi, THF, -78 ˚C
Me
O
Me
Cl H
O
Br2, CH2Cl2;
Et3N, 77%
H
Me
Me
Me H
Br
Me
O
Paquette and Geng's entrance into the triquinane nucleus-
H
H H
Me
75%
Me H
O
Me
H
H
Synthesis of dimethyllithio ketal lithio vinyl ether fragments
iPrO
iPrO
HO Me
ceratopicanol
O
MsCl, Et3N,
DMAP 72%
LiAlH4
THF;
1N HCl
76%
H
Me NaBH4, MeOH
Me
Me H
MOMCl,
N(iPr)2Et
quant.
H
O Me
Li, NH3
77%
Me
21% from s.m.
iPrO
-78 ˚C;
LiCH=CH2
0 ˚C;
NH4Cl
H
O
Me 10% H2SO4
Me
H
H
Me
Me
O
O Me
Me
OMOM
95%
H
H
MeLi, Et2O;
H
Me 30% H SO
2
4
iPrO
O
Me H
Me
OMOM
THF, 85%
Me
O
Me
Me
O
O
iPrO
iPrO
Me H
Me
iPrO
O
O
O
OiPr
O
OH
O
iPrO
O
Me
Me H
hypnophilin
+
Me
K2CO3, 30% H2O2
80% b.r.s.m. O
OH
O
O
HO
H
Me
O
O
iPrO
OH
H
O
iPrO
iPrO
LDA, DMPU, TMSCl;
Pd(OAc)2, MeCN
60%
O
O
Li
O
Me
Me H
O
iPrO
OH
O
O
O
(Tatsuta's precursor to coriolin)
OMe
Me
Li
iPrO
O
O Me
Me
O
O Me
Li
73%
iPrO
44%
OH
O Me
Me H
Me
Me
iPrO
iPrO
Cl
iPrO
O Me
Me
Me
Me
Li, NH3
75%
O
Me
iPrO
H
Me H2, 5% Pd/C
91%
H
iPrO
H
Me
iPrO
H
Me
H
Me
iPrO
OH
O
iPrO
O
O
iPrO
OH
Me
Li, NH3;
CH3I, HMPA
H
iPrO
O Me
CH3SO2Cl
Me DMAP, pyr.
iPrO
iPrO
H
Me
iPrO
iPrO
OH
Me
O
OH
O
O
O
iPrO
iPrO
OH
O
O
John Gallagher gratefully adknowledges and thanks the Evan's Group for their website and the information pertaining to Professor Wender and Curran's synthesese of coriolin.
Syntheses of coriolin•Paquette, Leo A.; Geng, Feng. Applications of the Squarate Ester Cascade to the Expeditious Synthesis of Hypnophilin, Coriolin, and Ceratopicanol. Journal of the American Chemical Society (2002),
124(31), 9199-9203.
• Tanino, Keiji. Development of new reactions for carbon-carbon bond formation by using carbocation species. Yuki Gosei Kagaku Kyokaishi (2001), 59(6), 549-559.
• Mehta, Goverdhan; Reddy, D. Srinivasa. A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)coronafacic acid and a formal synthesis of (+)-coriolin. Journal of the Chemical Society, Perkin Transactions 1 (2001), (10), 1153-1161.
• Little, R. Daniel; Ott, Michael M. A diradical route to bioactive natural products and their analogs. Studies in Natural Products Chemistry (2000), 22(Bioactive Natural Products (Part C)), 195-243.
• Singh, V.; Samanta, B.; Kane, V. V. Molecular complexity from aromatics: synthesis and photoreaction of endo-tricyclo[5.2.2.02,6]undecanes. Formal total syntheses of (±)-coriolin. Tetrahedron (2000),
56(39), 7785-7795.
• Singh, Vishwakarma; Alam, S. Q. Intramolecular diels-alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4-one and sigmatropic shifts in excited states: novel route to sterpuranes and linear triquinanes: formal total
synthesis of (±)-coriolin. Chemical Communications (Cambridge) (2000), (4), 319.
• Singh, Vishwakarma; Alam, S. Q. Intramolecular Diels-Alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4-one and sigmatropic shifts in excited states: novel route to sterpuranes and linear triquinanes: formal total
synthesis of (±)-coriolin. Chemical Communications (Cambridge) (1999), (24), 2519-2520.
• Mizuno, Hajime; Domon, Kei; Masuya, Keiichi; Tanino, Keiji; Kuwajima, Isao. Total Synthesis of (-)-Coriolin. Journal of Organic Chemistry (1999), 64(8), 2648-2656. Singh, Vishwakarma; Samanta, Biswajit.
Generation of molecular complexity from aromatics: a formal total synthesis of coriolin from 6-methylsaligenin. Tetrahedron Letters (1999), 40(2), 383-386.
• Singh, Vishwakarma; Thomas, Beena; Vedantham, Punitha. Aromatics to triquinanes. Synthesis of 1,4,4,11-tetramethyltricyclo[6.3.0.02,6]undeca-3,7,10-trione: a potential precursor for coriolin and congeners.
Tetrahedron (1998), 54(23), 6539-6552.
• Domon, Kei; Masuya, Keiichi; Tanino, Keiji; Kuwajima, Isao. Highly efficient method for coriolin synthesis. Tetrahedron Letters (1997), 38(3), 465-468.
• Tanino, Keiji; Domon, Kei; Takahashi, Yoshinori; Masuya, Keiichi; Kuwajima, Isao. A new synthetic method for cyclopentanes via formal [3+2] cycloaddition reaction. An efficient approach for triquinane
sesquiterpene frameworks. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1996), 38th 583-588.
• Weinges, Klaus; Braun, Ralf; Huber-Patz, Ursula; Irngartinger, Hermann. Radical-type cyclization of dienes. VI. Total synthesis of (-)-coriolin and (-)-epicoriolin from (S)-(+)-carvone. Liebigs Annalen der
Chemie (1993), (10), 1133-40.
• Toyta, Masahiro; Nishikawa, Youichi; Motoki, Kayoko; Yoshida, Naomi; Fukumoto, Keiichiro. Pd2+-promoted cyclization in linear triquinane synthesis. Total synthesis of (±)-hirsutene. Tetrahedron Letters
(1993), 34(38), 6099-102.
• Oppolzer, Wolfgang; Ando, Akira. Formal synthesis of (±)-coriolin by diastereocontrolled nickel(0)-catalyzed metallo-ene-type cyclization/methoxycarbonylation. Chimia (1992), 46(4), 122-5.
• Fevig, Thomas L.; Elliott, Richard L.; Curran, Dennis P. A samarium(II) iodide promoted tandem radical cyclization. The total synthesis of (±)-hypnophilin and the formal synthesis of (±)-coriolin. Journal of the
American Chemical Society (1988), 110(15), 5064-7.
• Van Hijfte, Luc; Little, R. Daniel; Petersen, Jeffrey L.; Moeller, Kevin D. Intramolecular 1,3-diyl trapping reactions. Total synthesis of (±)-hypnophilin and (±)-coriolin. Formation of the trans-fused
bicyclo[3.3.0]octane ring system. Journal of Organic Chemistry (1987), 52(21), 4647-61.
• Van Hijfte, Luc; Little, R. Daniel; Petersen, Jeffrey L.; Moeller, Kevin D. Intramolecular 1,3-diyl trapping reactions. Total synthesis of (±)-hypnophilin and (±)-coriolin. Formation of the trans-fused
bicyclo[3.3.0]octane ring system. Journal of Organic Chemistry (1987), 52(21), 4647-61
• Magnus, Philip; Exon, Christopher; Albaugh-Robertson, Pamela. Dicobalt octacarbonyl-alkyne complexes as intermediates in the synthesis of bicyclo[3.3.0]octenones for the synthesis of coriolin and hirsutic
acid. Tetrahedron (1985), 41(24), 5861-9.
• Funk, Raymond L.; Bolton, Gary L.; Daggett, Joy Umstead; Hansen, Marvin M.; Horcher, Linus H. M. Intramolecular cycloaddition reactions of exocyclic nitrones. Application in the total synthesis of terpenes.
Tetrahedron (1985), 41(17), 3479-95.
• Demuth, Martin; Ritterskamp, Peter; Weigt, Eva; Schaffner, Kurt. Total synthesis of (-)-coriolin. Journal of the American Chemical Society (1986), 108(14), 4149-54.
• Mehta, Goverdhan; Murthy, A. Narayana; Reddy, D. Sivakumar; Reddy, A. Veera. A general approach to linearly fused triquinane natural products. Total syntheses of (±)-hirsutene, (±)-coriolin, and (±)capnellene. Journal of the American Chemical Society (1986), 108(12), 3443-52.
• Van Hijfte, Luc; Little, R. Daniel. Intramolecular 1,3-diyl trapping reactions. A formal total synthesis of (±)-coriolin. Journal of Organic Chemistry (1985), 50(20), 3940-2.
• Demuth, Martin; Ritterskamp, Peter; Schaffner, Kurt. Novel variant of the tricyclooctanone approach to cyclopentanoid natural products. Synthesis of (±)-coriolin. Preliminary communication. Helvetica
Chimica Acta (1984), 67(7), 2023-7.
• Schuda, Paul Francis; Heimann, Martha R. The synthesis of dl-coriolin. Tetrahedron (1984), 40(12), 2365-80.
• Wender, P. A.; Howbert, J. J. Synthetic studies on areneolefin cycloadditions - VI. Two syntheses of (±)-coriolin. Tetrahedron Letters (1983), 24(48), 5325-8.
• Schuda, Paul Francis; Heimann, Martha R. The synthesis of dl-coriolin. Tetrahedron Letters (1983), 24(40), 4267-70
• Mehta, Goverdhan; Reddy, A. Veera; Murthy, A. Narayana; Reddy, D. Sivakumar. A total synthesis of (±)-coriolin. Journal of the Chemical Society, Chemical Communications (1982), (10), 540-1.
• Exon, Christopher; Magnus, Philip. Stereoselectivity of intramolecular dicobalt octacarbonyl alkene-alkyne cyclizations: short synthesis of dl-coriolin. Journal of the American Chemical Society (1983),
105(8), 2477-8.
• to, Toshio; Tomiyoshi, Nobuya; Nakamura, Koki; Azuma, Shizuo; Izawa, Makoto; Maruyama, Fumio; Yanagiya, Mitsutoshi; Shirahama, Haruhisa; Matsumoto, Takeshi. A new synthesis of dl-coriolin A.
Application of a new SN2 reaction at a neopentylic position. Tetrahedron Letters (1982), 23(16), 1721-4.
• Schuda, Paul F.; Ammon, Herman L.; Heimann, Martha R.; Bhattacharjee, Sovan. Synthesis of coriolin. An approach to a functionalized BC ring system. Journal of Organic Chemistry (1982), 47(18), 343440.
• Tatsuta, Kuniaki; Akimoto, Kohji; Kinoshita, Mitsuhiro. The total synthesis of (±)-coriolin. Tetrahedron (1981), 37(25), 4365-9.
• Iseki, Katsuhiko; Yamazaki, Mayumi; Shibasaki, Masakatsu; Ikegami, Shiro. The total synthesis of dl-coriolin. Tetrahedron (1981), 37(25), 4411-18.
• Trost, Barry M.; Curran, Dennis P. Synthesis of dl-coriolin. Journal of the American Chemical Society (1981), 103(24), 7380-1.
• Danishefsky, Samuel; Zamboni, Robert; Kahn, Michael; Etheredge, Sarah Jane. Total synthesis of dl-coriolin. Journal of the American Chemical Society (1980), 102(6), 2097-8.
• Shibasaki, Masakatsu; Iseki, Katsuhiko; Ikegami, Shiro. A total synthesis of dl-coriolin. Tetrahedron Letters (1980), 21(37), 3587-90.
• Tatsuta K; Akimoto K; Kinoshita M The total synthesis of (+/-)-coriolin. Journal of antibiotics (1980 Jan), 33(1), 100-2.