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Enantioselective Total Synthesis of (−)-Incarviatone A

Author:
Hong Benke, Li Chao, Wang Zhen, Chen Jie, Li Houhua, Lei Xiaoguang
Source:
Journal of the American Chemical Society 2015 v.137 no.37 pp. 11946-11949
ISSN:
1520-5126
Subject:
biomimetics, chemical reactions, enantiomers, mechanistic models, phenylacetic acid, synthesis
Abstract:
We report herein the first total synthesis of (−)-incarviatone A (1) in 14 steps starting from commercially available inexpensive phenylacetic acid (9). Our early stage synthesis relies on the scalable and sequential C–H functionalization to rapidly assemble the indanyl dialdehyde framework. Further biomimetic cascade strategy allows us to obtain the natural product in a one-pot operation. We also conduct detailed mechanistic studies and disclose all the possible intermediates and isomers formed during the biomimetic cascade process.
Agid:
5416246