期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 35, 页码 10483-10486出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604770
关键词
aldol reactions; alkaloids; natural products; rearrangements; total synthesis
资金
- Tsinghua University
- 1000 Talents Recruitment Program
- Collaborative Innovation Center for Biotherapy (Tsinghua University)
- Collaborative Innovation Center for Biotherapy (Sichuan University)
Reported herein is the total synthesis of calophyline A, an indoline natural product possessing distinct ring connectivity which has not been synthesized previously. The synthetic route features several key transformations, including an aza-pinacol rearrangement to construct the nitrogen-containing bridged [3.2.2] bicycle, a Heck cyclization to assemble the fused 6/5/6/5 ring system, and a challenging late-stage aldol reaction to generate both a neopentyl quaternary stereogenic center and an oxygen-containing bridged [3.2.1] bicycle.
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