Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition

Xuelei Jia; Honghui Lei; Feipeng Han; Tao Zhang; Ying Chen; Zhengshuang Xu; Pratanphorn Nakliang; Sun Choi; Yian Guo; Tao Ye

doi:10.1002/anie.202005048

Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl₂-Catalyzed Intramolecular [3+2] Cycloaddition

Xuelei Jia, Honghui Lei, Feipeng Han, Tao Zhang, Ying Chen, Zhengshuang Xu, Pratanphorn Nakliang, Sun Choi, Yian Guo, Tao Ye

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl₂-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

Original language	English
Pages (from-to)	12832-12836
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	31
DOIs	https://doi.org/10.1002/anie.202005048
State	Published - 27 Jul 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Pt catalysis
[3+2] cycloaddition reactions
alkaloids
kopsanes
natural products

Access to Document

10.1002/anie.202005048

Cite this

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title = "Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition",

abstract = "A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.",

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T1 - Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition

AU - Jia, Xuelei

AU - Lei, Honghui

AU - Han, Feipeng

AU - Zhang, Tao

AU - Chen, Ying

AU - Xu, Zhengshuang

AU - Nakliang, Pratanphorn

AU - Choi, Sun

AU - Guo, Yian

AU - Ye, Tao

PY - 2020/7/27

Y1 - 2020/7/27

N2 - A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

AB - A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2-catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation.

KW - Pt catalysis

KW - [3+2] cycloaddition reactions

KW - alkaloids

KW - kopsanes

KW - natural products

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