A short synthesis of (±)-13-deoxyserratine

J. Cassayre (1) , Fabien Gagosz (2) , Samir Z. Zard (2)

1 Syngenta AG Suisse
2 DCSO - Laboratoire de synthèse organique

A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.

Domaines: Chimie organique

J. Cassayre, Fabien Gagosz, Samir Z. Zard. A short synthesis of (±)-13-deoxyserratine. Angewandte Chemie International Edition, 2002, 41 (10), pp.1783-1785. ⟨10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I⟩. ⟨hal-00954852⟩