Asymmetric total synthesis of (−)-δ-lycorane. Issue 6 (10th March 2017)

• Record Type: Journal Article
• Authors: Wang, Junliang; Li, Jianneng; Shen, Xianwang; Dong, Cong; Lin, Jun; Wei, Kun
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 6(2017)
• Page Start: 1149
• Page End: 1152
• Publication Date: 2017-03-10
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00021a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A first asymmetric synthesis of (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction is reported. 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.