Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 2, Issue 14, Pages 2050-2060Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b401829j
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An eleven-step synthesis of the title compound ( 1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)- 9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone, 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.
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