期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 30, 页码 10168-10172出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201906039
关键词
biomimetic synthesis; cyclization; diastereoselectivity; natural products; terpenoids
资金
- JSPS KAKENHI [JP20310137]
- Asahi Glass Foundation
Biomimetic epoxide-opening cascades of polyepoxides enable the efficient and rapid construction of polyether frameworks. Herein, we show that the epoxide-opening cascade cyclization that affords tetrahydrofuran products in acidic aqueous media produces tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far. The novel cascade cyclization in H2O was applied to the synthesis of a new nerolidol-type sesquiterpenoid, resulting in revision of the proposed structure and determination of the absolute configuration.
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