Abstract
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 α-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.
| Original language | English |
|---|---|
| Pages (from-to) | 7128-7133 |
| Number of pages | 6 |
| Journal | Organic Letters |
| Volume | 24 |
| Issue number | 39 |
| DOIs | |
| Publication status | Published - 2022 Oct 7 |
Bibliographical note
Funding Information:This study was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government {NRF-2021R1A2C1012984 and NRF-2021R1A5A6002803, (Center for New Directions in Organic Synthesis)}. J.J. acknowledges the financial support from the NRF-2018 Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program funded by the Korean Government. We dedicated this work to Professor Jung-Il Jin on the occasion of his 80th birthday.
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry