Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B

Ken S. Feldman, Joe C. Saunders, Michelle Laci Wrobleski

Research output: Contribution to journalArticle

73 Scopus citations

Abstract

The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium salt → alkylidenecarbene → cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

Original languageEnglish (US)
Pages (from-to)7096-7109
Number of pages14
JournalJournal of Organic Chemistry
Volume67
Issue number20
DOIs
StatePublished - Oct 4 2002

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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