Synthesis of the C12–C24 fragment of peloruside A by silyl-tethered diastereomer-discriminating RCM

EM Casey, P Teesdale-Spittle, JE Harvey

Index: Casey, Emma M.; Teesdale-Spittle, Paul; Harvey, Joanne E. Tetrahedron Letters, 2008 , vol. 49, # 49 p. 7021 - 7023

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Citation Number: 24

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 ...