期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 28, 页码 8187-8190出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703803
关键词
C-H activation; carbenoids; hydrogen-atom transfer; natural products; rhodium
资金
- Natural Science Foundation of China [21572187, U1405228, 21272194, 21142007]
- FRFCU [20720160025]
- NFFTBS [J1310024]
- NCETFJ
A concise, protecting-group-free total synthesis of the unusual brominated sesquiterpene aplydactone is described. Our synthesis features a [2+2] photocycloaddition, a Wolff ring contraction, an unusual remote C-H functionalization to establish the highly strained tetracyclic core, and a hydrogen-atom transfer (HAT) reaction to access the bromine-containing stereocenter. A finely tuned conformation of the a-diazoketone precursor is the key for the success of the late-stage transannular C-H insertion to deliver a bridged six-membered ring and a quaternary stereocenter (C6) between two quaternary carbon atoms (C1 and C7).
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