期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 41, 页码 13778-13789出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja804939r
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资金
- National Institutes of Health (National Cancer Institute) [CA19033]
- Merck Co., Inc.
A full account of the enantioselective total syntheses of (+)-lyconadin A (1) and (-)-lyconadin B (2) is presented. Central to this venture was recognition and deployment of a key strategy-level intramolecular aldol/conjugate addition cascade that led, in a single operation, to two new carbon-carbon sigma-bonds, three new stereogenic centers, and two new rings, albeit with the incorrect stereogenicity at C(12) for the lyconadins. Correction of the C(12) stereogenicity was achieved via innovative use of a protonated intramolecular aminal. An aminoiodo olefin cyclization, in conjunction with a-pyridinone and 3,4-dihydropyridinone annulation protocols, permitted completion of the syntheses of (+)-lyconadin A (1) and (-)-lyconadin B (2), respectively.
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