Concise Total Synthesis of (+)

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Concise Total Synthesis of
(+)-Lyconadin A
Research by: Tohru Fukuyama
Presentation by: Carl Brothers
Tohru Fukuyama
• Chemistry Professor at
University of Tokyo in
Japan
– Graduate school of
Pharmaceutical Sciences
– Synthetic Natural Products
chemistry
• Discovered Fukuyama
Coupling in 1998
Fukuyama Coupling
• Coupling between a thioester and an
organozinc halide in the presence of a
palladium catalyst.
– Mild reaction conditions
– High chemoselectivity
– Less toxic reagents
– Stops at ketone
(+)-Lyconadin A
– Cytotoxic to murine
lymphoma L1210
cells and KB cells.
– Enhances mRNA
expression for nerve
growth factor in
astrocytoma cells.
– Found in
Lycopodium
complanatum.
Lycopodium complanatum
(AKA. Northern Ground Cedar)
• Club Moss family
• Ground level creeping evergreen found in acidic soils
of wooded areas and rocky slopes in North America
and Europe.
• Previously used to
make a medicinal
tea which would
increase urine
production,
stimulate
menstrual flow,
and relieve
spasms.
Retrosynthetic Analysis
Lab
D-A
Ring expansion
Forward Synthesis
DA
Reductive
amin
aza -prins
Dibromo
cyclo prop
Ring
expansion
Treatment of 11 with diphenyl
disulfide
Vinylogous
pummer
Treatment of 11 with isoamyl
nitrite
Michael
•8.1% overall yield by nitrosoalkene method.
•11.6% overall yield by sulfide method.
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