Applications of Organosulfur Chemistry to Organic Synthesis: Total Synthesis of (+)-Himbeline and (+)-Himbacine

Abstract

Total syntheses of (+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia−Lythgoe olefination. The preparation of sulfone 38 features an acid-promoted intramolecular Diels−Alder reaction of an α,β-unsaturated thioester while the synthesis of 42 features a Beak alkylation of piperidine 39.