Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy

Scott E Denmark, Jack Hung Chang Liu, Joseck M. Muhuhi

Research output: Contribution to journalArticle

Abstract

Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

Original languageEnglish (US)
Pages (from-to)201-215
Number of pages15
JournalJournal of Organic Chemistry
Volume76
Issue number1
DOIs
StatePublished - Jan 7 2011

ASJC Scopus subject areas

  • Organic Chemistry

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