Radical-mediated diastereoselective construction of a chiral synthon for synthesis of dolabellanes.
[reaction: see text] A useful trans-substituted multifunctional cyclopentane with a chiral quaternary center was selectively synthesized by free radical Michael addition to the (Z)-propionate or -malonate derivatives. The stereoselectivity could be reversed by changing the configuration of the double bond.
Zhu
Q
Q
State Key Laboratory of Bio-organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Fan
K Y
KY
Ma
H W
HW
Qiao
L X
LX
Wu
Y L
YL
Wu
Y
Y