Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
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Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
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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
2021Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
1523-7052