Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine

David J. Hart, Jing Li, Wen Lian Wu, Alan P. Kozikowski

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)5023-5033
Number of pages11
JournalJournal of Organic Chemistry
Volume62
Issue number15
DOIs
StatePublished - Jul 25 1997

ASJC Scopus subject areas

  • Organic Chemistry

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