Synthesis of the C12-C24 fragment of peloruside A by silyl-tethered diastereomer-discriminating RCM |
| |
Authors: | Emma M. Casey |
| |
Affiliation: | School of Chemical and Physical Sciences and School of Biological Sciences, Centre for Biodiscovery, Victoria University of Wellington, PO Box 600, Wellington, New Zealand |
| |
Abstract: | The C12-C24 fragment of peloruside A has been synthesized using, as a key step, a silyl-tethered ring closing metathesis reaction to form the C16-C17 (Z)-alkene. The metathesis reaction discriminates between diastereoisomers of the starting material. A diphenylsilyl bis-ether provides simultaneous protection for the C15 and C24 hydroxyl groups, and is expected to lead to high 1,5-anti selectivity in subsequent aldol reactions of the methyl ketone, allowing for a convergent stereoselective synthesis of peloruside A. |
| |
Keywords: | Metathesis Stereoselectivity Silyl tether Natural product synthesis |
本文献已被 ScienceDirect 等数据库收录! |
|