Notice
This is not the latest version of this item. The latest version can be found at:https://dspace.mit.edu/handle/1721.1/141145.2
Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
DownloadSubmitted version (701.6Kb)
Open Access Policy
Open Access Policy
Creative Commons Attribution-Noncommercial-Share Alike
Terms of use
Metadata
Show full item recordAbstract
We report the first total synthesis of (-)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. The vinylogous urethane substructure of this intermediate affords (-)-kopsifoline D via C3-C21 bond formation under the Mitsunobu reaction conditions, while it enables selective C17-functionalization en route to (-)-kopsifoline A and (+)-kopsifoline E.
Date issued
2021-12-03Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Myeong, In-Soo, Avci, Nadide Hazal and Movassaghi, Mohammad. 2021. "Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E." Organic Letters, 23 (23).
Version: Original manuscript