A Short Synthesis of (±)-Matrine

Laurent Boiteau; Jean Boivin; Annie Liard; Béatrice Quiclet-Sire; Samir Z Zard

doi:10.1002/(SICI)1521-3773(19980504)37:8<1128::AID-ANIE1128>3.0.CO;2-P

A Short Synthesis of (±)-Matrine

Angew Chem Int Ed Engl. 1998 May 4;37(8):1128-1131. doi: 10.1002/(SICI)1521-3773(19980504)37:8<1128::AID-ANIE1128>3.0.CO;2-P.

Authors

Laurent Boiteau¹, Jean Boivin¹, Annie Liard², Béatrice Quiclet-Sire², Samir Z Zard²

Affiliations

¹ Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex (France), Fax: (+33) 1 69-33-30-10.
² Institut de Chimie des Substances Naturelles, F-91198 Gif-Sur-Yvette (France), Fax: (+33) 1 69-07-72-47.

Abstract

Three different radical reactions were used in a short total synthesis of (±)-matrine (1). Two of the four six-membered rings and four new bonds were created in one radical cascade involving intermolecular addition followed by two successive cyclizations and transfer of a xanthate group.

Keywords: Cyclizations; Domino reactions; Matrine; Natural products; Radical reactions.