Total synthesis of (-)-sarain A

Michael H. Becker, Peter Chua, Robert Downham, Christopher J. Douglas, Neil K. Garg, Sheldon Hiebert, Stefan Jaroch, Richard T. Matsuoka, Joy A. Middleton, Fay W. Ng, Larry E. Overman

Research output: Contribution to journalArticlepeer-review

83 Scopus citations

Abstract

This article describes the details of our synthetic studies toward the complex marine alkaloid sarain A. Various strategies were conceived, setbacks encountered, and solutions developed, ultimately leading to a successful enantioselective total synthesis. Our route to (-)-sarain A features a number of key steps, including an asymmetric Michael addition to install the C4′-C3′-C7′ stereotriad, an enoxysilane-N-sulfonyliminium ion cyclization to set the C3 quaternary carbon stereocenter, and assemble the diazatricycloundecane core, a ring-closing metathesis to construct the 13-membered ring, an intramolecular Stille coupling to fashion the unsaturated 14-membered macrocycle, and a late-stage installation of the tertiary amine-aldehyde proximity interaction.

Original languageEnglish (US)
Pages (from-to)11987-12002
Number of pages16
JournalJournal of the American Chemical Society
Volume129
Issue number39
DOIs
StatePublished - Sep 12 2007

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