Massachusetts Institute of Technology
Organic Chemistry 5.512
April 4, 2005
Prof. Rick L. Danheiser
Problem Set 4
Practice Problems for First Exam
Design a highly stereoselective synthesis of the following target molecules beginning with commercially
available materials. Be sure to explicitly identify all reagents necessary for each transformation.
Enantiomerically enriched reagents may be used if they are commercially available; however, each
stereogenic center in the target molecule must be generated in your synthetic route. In other words, the
stereogenic carbons in the chiral reagents you employ cannot be directly incorporated in the final product.
O
(1)
(2)
CN
Br
O
(3)
(4)
O
OH
OMe
(5)
O
H
(6)
N
H
H
OBn
(7)
(8)
O
Ph
O
OH
O
(9)
OH
Ph
H
OH
(10)
H
(11)
O
O
t-BuMe2SiO
(12)
CO2Me
F
F
O
(13)
O
O
OMe
O
(14)
O
NH2
(15)
O
(16)
O
H
CH3
O
(17)
OCH2OMe
(18)
CO2Me
NEt2
(19)
H
(20)
N
OH
(21)
MeO2C