Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 8, Pages 5727-5743Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00209
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Funding
- National Natural Science Foundation of China [21822304]
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The palladium-catalyzed intramolecular dearomative Heck reaction is an efficient method for synthesizing spiro-indoline products. It involves the reaction of simple 2,3-disubstituted indoles with subsequent aza-semipinacol rearrangement to construct specific core structures. This approach has been successfully applied to accomplish the formal total synthesis of akuammiline alkaloids vincorine.
The palladium-catalyzed intramolecular dearomative Heck reaction of 2,3-disubstituted indoles serves as an access to spiro-indoline products. Herein, we report an efficient construction of indoline/indolenine core stuctures via a dearomative Heck reaction of simple 2,3-disubstituted indoles with all-carbon tethers and the subsequent aza-semipinacol rearrangement. The Heck reaction features a high C2-selectivity, and the stereospecific aryl/alkyl migration selectivity has been investigated by DFT calculations. Using this method, we accomplished the formal total synthesis of akuammiline alkaloids vincorine.
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