Sequencing of three-component olefin metatheses: Total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin

Thomas R. Hoye, Brian M. Eklov, Junha Jeon, Mila Khoroosi

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

An efficient, flexible, and highly convergent strategy for accessing skipped bis-THF containing Annonaceous acetogenins is demonstrated by the synthesis of each of (+)-gigantecin (1) and its constitutional isomer (+)-14-deoxy-9-oxygigantecin (11). The skeleton of each compound is produced, at will, from the same precursors via a three-component ring-closing/cross- metathesis sequence that differs only in the ordering of the RCM vs CM events. Another notable aspect is the use of in situ epoxide-closing and -opening of iodohydrins with dimethylsulfonium methylide to provide inverted allylic alcohols.

Original languageEnglish (US)
Pages (from-to)3383-3386
Number of pages4
JournalOrganic Letters
Volume8
Issue number15
DOIs
StatePublished - Jul 20 2006

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