Journal
ORGANIC LETTERS
Volume 24, Issue 39, Pages 7128-7133Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02788
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Funding
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2021R1A2C1012984, NRF2021R1A5A6002803]
- Future Basic Science Program/Global Ph.D. Fellowship Program - Korean Government
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In this paper, the first asymmetric total synthesis of iheyamine B from 2,2'-bisindoloazepinone is reported, which involves the stereoselective construction of the trans-vicinal 2-oxopropyl moiety in the azepine scaffold.
Herein, we report the first asymmetric total synthesis of iheyamine B from 2,2 '-bisindoloazepinone using the stereoselective construction of the trans-vicinal 2-oxopropyl moiety in the azepine scaffold. The asymmetric decarboxylative allylic alkylation provided the alpha- allylated 2,2 '-bisindoloazepinone intermediate. The subsequent conversion of the lactam moiety into another allyl group in a trans-selective manner followed by Wacker oxidation of each allyl unit to the corresponding 2-oxopropyl group completed the total synthesis of iheyamine B.
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