Jump to main content
Jump to site search

Issue 6, 2017
Previous Article Next Article

Asymmetric total synthesis of (−)-δ-lycorane

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Jan 2017, accepted on 01 Mar 2017 and first published on 02 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00021A
Citation: Org. Chem. Front., 2017,4, 1149-1152
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements