期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 39, 页码 11987-12002出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja074300t
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资金
- NCI NIH HHS [CA-76739] Funding Source: Medline
- NHLBI NIH HHS [HL-80901, HL-25854] Funding Source: Medline
- NIGMS NIH HHS [GM-79922] Funding Source: Medline
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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