Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide

Arun K. Ghosh, Luke A. Kassekert

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Both epimers at C-21 in the proposed structure of (+)-callyspongiolide have been synthesized in a convergent and enantioselective manner. The 14-membered macrolide with a sensitive C2-C3 cis-olefin functionality was installed by a Yamaguchi macrolactonization of hydroxyl alkynoic acid followed by hydrogenation over Lindlar's catalyst. The C5 methyl stereocenter was constructed by a ring-closing olefin metathesis followed by addition of methyl cuprate to an α,β-unsaturated I-lactone. Other key reactions are chiral Corey-Bakshi-Shibata (CBS) reduction and Sonogashira coupling to conjoin the macrocyclic core and side chain.

Original languageEnglish (US)
Pages (from-to)3274-3277
Number of pages4
JournalOrganic Letters
Volume18
Issue number13
DOIs
StatePublished - Jul 1 2016

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