A Novel and Highly Stereoselective Intramolecular Formal [3+3] Cycloaddition Reaction of Vinylogous Amides Tethered with α,β-Unsaturated Aldehydes: A Formal Total Synthesis of (+)-Gephyrotoxin

Lin-Li Wei; Richard P Hsung; Heather M Sklenicka; Aleksey I Gerasyuto

doi:10.1002/1521-3773(20010417)40:8<1516::AID-ANIE1516>3.0.CO;2-V

A Novel and Highly Stereoselective Intramolecular Formal [3+3] Cycloaddition Reaction of Vinylogous Amides Tethered with α,β-Unsaturated Aldehydes: A Formal Total Synthesis of (+)-Gephyrotoxin

Angew Chem Int Ed Engl. 2001 Apr 17;40(8):1516-1518. doi: 10.1002/1521-3773(20010417)40:8<1516::AID-ANIE1516>3.0.CO;2-V.

Authors

Lin-Li Wei¹, Richard P Hsung¹, Heather M Sklenicka¹, Aleksey I Gerasyuto¹

Affiliation

¹ Department of Chemistry, University of Minnesota Minneapolis, MN, 55455 (USA) Fax: (+1) 612-626-7541.

PMID: 29712373
DOI: 10.1002/1521-3773(20010417)40:8<1516::AID-ANIE1516>3.0.CO;2-V

Abstract

Complex piperidinyl heterocycles (for example, 2) were accessed by using a novel intramolecular formal [3+3] cycloaddition reaction of vinylogous amides tethered with enals (for example, 1). This method has been applied to a formal total synthesis of (+)-gephyrotoxin (3).

Keywords: alkaloids; amides; cycloaddition; electrocyclic reactions; synthetic methods.