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 journalArticle

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
Externally publishedYes

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Sulfones
Enantiomers
Alkylation
Aldehydes
Acids
himbacine
piperidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Applications of organosulfur chemistry to organic synthesis : Total synthesis of (+)-himbeline and (+)-himbacine. / Hart, David J.; Li, Jing; Wu, Wen Lian; Kozikowski, Alan P.

In: Journal of Organic Chemistry, Vol. 62, No. 15, 25.07.1997, p. 5023-5033.

Research output: Contribution to journalArticle

Hart, David J. ; Li, Jing ; Wu, Wen Lian ; Kozikowski, Alan P. / Applications of organosulfur chemistry to organic synthesis : Total synthesis of (+)-himbeline and (+)-himbacine. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 15. pp. 5023-5033.
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