Total synthesis of (-)-sarain A |
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Authors: | Becker Michael H Chua Peter Downham Robert Douglas Christopher J Garg Neil K Hiebert Sheldon Jaroch Stefan Matsuoka Richard T Middleton Joy A Ng Fay W Overman Larry E |
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Institution: | Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA. |
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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. |
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