期刊
TETRAHEDRON
卷 73, 期 34, 页码 5063-5071出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.06.050
关键词
Chromene; Benzyne; Furan; Quinone; Enzymatic kinetic resolution; Diels-Alder reaction
资金
- Uehara Memorial Foundation
- Musashino Joshi-Gakuin
We report the asymmetric total syntheses of teretifolione B and methylteretifolione B, which are benzochromenes originally isolated from Conospermum plants. The synthesis involves enzymatic asymmetric transesterification of racemic acetoxychromene and construction of the basic framework via Diels-Alder reaction of optically active pyranobenzyne and substituted furans. The absolute configuration of the chiral chromene was unambiguously determined by asymmetric total synthesis of teretifolione B and its characterization. The first asymmetric total synthesis of methylteretifolione B was achieved in a similar manner and its absolute configuration, for which direct proof has not been reported, was established. (C) 2017 Elsevier Ltd. All rights reserved.
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