Issue 6, 2017

Asymmetric total synthesis of (−)-δ-lycorane

Abstract

A first asymmetric synthesis of the lycorine-type Amaryllidaceae alkaloid (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction as a powerful tool to construct the skeleton of the alkaloid on the basis of unsaturated β-ketoester and nitroalkene is reported. The sequence afforded a highly functionalized intermediate with three stereogenic centres with high diastereoselectivity (>20 : 1 dr) and high enantioselectivity (92% ee) in one step, which was converted into (−)-δ-lycorane in eight steps.

Graphical abstract: Asymmetric total synthesis of (−)-δ-lycorane

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jan 2017
Accepted
01 Mar 2017
First published
02 Mar 2017

Org. Chem. Front., 2017,4, 1149-1152

Asymmetric total synthesis of (−)-δ-lycorane

J. Wang, J. Li, X. Shen, C. Dong, J. Lin and K. Wei, Org. Chem. Front., 2017, 4, 1149 DOI: 10.1039/C7QO00021A

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