Issue 3, 2024

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Abstract

The first asymmetric total syntheses of (+)-pancratinines B and C and the asymmetric total syntheses of (−)-montanine, (−)-pancracine and (−)-brunsvigine were realized in a divergent fashion. Our synthetic strategy features a copper-catalyzed [3 + 2] annulation reaction, Pictet–Spengler cyclization and an epoxide opening and hydroxyl elimination to form the challenging C1[double bond, length as m-dash]C11a bond.

Graphical abstract: Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Supplementary files

Article information

Article type
Research Article
Submitted
04 Nov. 2023
Accepted
01 Dec. 2023
First published
03 Dec. 2023

Org. Chem. Front., 2024,11, 668-672

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

F. Wang, X. Xu, Y. Yan, J. Zhang and Y. Yang, Org. Chem. Front., 2024, 11, 668 DOI: 10.1039/D3QO01835K

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