Issue 12, 2015

Concise total syntheses of (±)-mesembrane and (±)-crinane

Abstract

A straightforward and unified strategy to access Amaryllidaceae alkaloids comprising a cis-3a-aryloctahydroindole scaffold has been developed. The strategy features Eschenmoser–Claisen rearrangement of allylalcohol as a key step for the installation of all-carbon quaternary stereocenters present in these alkaloids. The consequent iodolactonization–reduction–oxidation sequence beautifully assembles the advanced intermediate keto-aldehyde 10a, b in synthetically viable yields. The methodology has been successfully applied in the efficient syntheses of (±)-mesembrane (1a) and (±)-crinane (2a).

Graphical abstract: Concise total syntheses of (±)-mesembrane and (±)-crinane

Supplementary files

Article information

Article type
Communication
Submitted
29 Jan 2015
Accepted
10 Feb 2015
First published
10 Feb 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 3585-3588

Concise total syntheses of (±)-mesembrane and (±)-crinane

M. K. Das, S. De, Shubhashish and A. Bisai, Org. Biomol. Chem., 2015, 13, 3585 DOI: 10.1039/C5OB00183H

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