Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E

Organic Letters
2021.0

Abstract

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. © 2021 American Chemical Society.

DOI： 10.1021/acs.orglett.1c03448

Knowledge Graph

Similar Paper

Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
Organic Letters 2021.0
Total Syntheses of Kopsaporine, Kopsinol and Kopsiloscine A
Angewandte Chemie International Edition 2023.0
Asymmetric Total Synthesis of Novel Pentacyclic Indole Alkaloid, Kopsiyunnanine E, Isolated from Kopsia arborea
Organic Letters 2014.0
Divergent Total Synthesis of Four Kopsane Alkaloids: N‐Carbomethoxy‐10,22‐dioxokopsane, Epikopsanol‐10‐lactam, 10,22‐Dioxokopsane, and N‐Methylkopsanone
Angewandte Chemie International Edition 2022.0
Asymmetric Total Synthesis of Kopsiyunnanine K, a Monoterpenoid Indole Alkaloid with a Rearranged Skeleton
Organic Letters 2016.0
Total Synthesis of Kopsinitarine E
Angewandte Chemie International Edition 2020.0
Divergent Total Syntheses of (−)-Pseudocopsinine and (−)-Minovincinine
The Journal of Organic Chemistry 2020.0
Asymmetric total synthesis of (−)-melotenine A
Tetrahedron 2016.0
Total synthesis of kopsine, fruticosine, and structurally related polycyclic caged Kopsia indole alkaloids
Organic Chemistry Frontiers 2020.0
First Asymmetric Total Syntheses of (−)-Subincanadines A and B, Skeletally Rearranged Pentacyclic Monoterpenoid Indole Alkaloids in Aspidosperma subincanum
Organic Letters 2006.0