Stereoselective synthesis of the C(1)-C(12) segment of iriomoteolide 1a: a very potent macrolide antitumor agent.
A stereoselective synthesis of the C(1)-C(12) segment of the potent cytotoxic macrolide, iriomoteolide 1a, has been accomplished. The key steps involve an enzymatic kinetic resolution of a β-hydroxy amide, a Pd-catalyzed cross-coupling to a substituted allylsilane, a highly regio- and stereoselective conjugate addition of lithium dimethylcopper to an α, β-acetylenic esters and an elaboration of the C(6)-C(7) trans-olefin geometry by a Julia-Kocienski olefination.
Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA.
Arun K
AK
Ghosh
Hao
H
Yuan