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

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

doi:10.1021/jo970612a

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

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

School of Medicine

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	5023-5033
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	62
Issue number	15
DOIs	https://doi.org/10.1021/jo970612a
State	Published - Jul 25 1997

ASJC Scopus subject areas

Organic Chemistry

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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.",

author = "Hart, {David J.} and Jing Li and Wu, {Wen Lian} and Kozikowski, {Alan P.}",

year = "1997",

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T1 - Applications of organosulfur chemistry to organic synthesis

T2 - Total synthesis of (+)-himbeline and (+)-himbacine

AU - Hart, David J.

AU - Li, Jing

AU - Wu, Wen Lian

AU - Kozikowski, Alan P.

PY - 1997/7/25

Y1 - 1997/7/25

N2 - 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.

AB - 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.

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