Enantioselective total synthesis and structural assignment of callyspongiolide

Arun K. Ghosh, Luke A. Kassekert, Joseph D. Bungard

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

We have elucidated the complete absolute configuration of callyspongiolide and unambiguously assigned its stereochemistry at the C-21 center through synthesis. Four stereoisomers of callyspongiolide were synthesized in a convergent and enantioselective manner. A late-stage Sonogashira coupling forges the diene-ynic side chain. Other notable reactions are Yonemitsu's variation of Yamaguchi macrolactonization to cyclize an alkynic seco acid, highly trans-selective Julia-Kocienski olefination, CBS reduction to set the C-21 stereocenter, and methyl cuprate addition to an unsaturated pyranone to install the C-5 methyl center.

Original languageEnglish (US)
Pages (from-to)11357-11370
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number48
DOIs
StatePublished - 2016

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

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