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

Research output: Contribution to journal › Article

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
Externally published	Yes

Fingerprint

Sulfones

Enantiomers

Alkylation

Aldehydes

Acids

himbacine

piperidine

ASJC Scopus subject areas

Organic Chemistry

Cite this

Hart, D. J., Li, J., Wu, W. L., & Kozikowski, A. P. (1997). Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine. Journal of Organic Chemistry, 62(15), 5023-5033. https://doi.org/10.1021/jo970612a

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 journal › Article

Hart, DJ, Li, J, Wu, WL & Kozikowski, AP 1997, 'Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine', Journal of Organic Chemistry, vol. 62, no. 15, pp. 5023-5033. https://doi.org/10.1021/jo970612a

Hart DJ, Li J, Wu WL, Kozikowski AP. Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine. Journal of Organic Chemistry. 1997 Jul 25;62(15):5023-5033. https://doi.org/10.1021/jo970612a

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.

@article{dca962fd918f4ffbb514cf99abe1f205,

title = "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.",

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

year = "1997",

month = "7",

day = "25",

doi = "10.1021/jo970612a",

language = "English (US)",

volume = "62",

pages = "5023--5033",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0030757959&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030757959&partnerID=8YFLogxK

U2 - 10.1021/jo970612a

DO - 10.1021/jo970612a

M3 - Article

AN - SCOPUS:0030757959

VL - 62

SP - 5023

EP - 5033

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

Access to Document

10.1021/jo970612a