Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman

Albert W.M. Lee; Wing Hong Chan; Yi Tao; Yu Kai Lee

doi:10.1039/p19940000477

Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman

Albert W.M. Lee^*, Wing Hong Chan, Yi Tao, Yu Kai Lee

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

35 Citations (Scopus)

Abstract

Michael addition of 2-(3,4-dirnethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity. Optically pure (R)-(+)-carnegineand (R)-(+)-tetrahydroharman have been synthesized.

Original language	English
Pages (from-to)	477-481
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	4
DOIs	https://doi.org/10.1039/p19940000477
Publication status	Published - 1994

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General Chemistry

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title = "Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman",

abstract = "Michael addition of 2-(3,4-dirnethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity. Optically pure (R)-(+)-carnegineand (R)-(+)-tetrahydroharman have been synthesized.",

author = "Lee, {Albert W.M.} and Chan, {Wing Hong} and Yi Tao and Lee, {Yu Kai}",

year = "1994",

doi = "10.1039/p19940000477",

language = "English",

pages = "477--481",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "4",

}

Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman. / Lee, Albert W.M.; Chan, Wing Hong; Tao, Yi et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 4, 1994, p. 477-481.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman

AU - Lee, Albert W.M.

AU - Chan, Wing Hong

AU - Tao, Yi

AU - Lee, Yu Kai

PY - 1994

Y1 - 1994

N2 - Michael addition of 2-(3,4-dirnethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity. Optically pure (R)-(+)-carnegineand (R)-(+)-tetrahydroharman have been synthesized.

AB - Michael addition of 2-(3,4-dirnethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity. Optically pure (R)-(+)-carnegineand (R)-(+)-tetrahydroharman have been synthesized.

UR - http://www.scopus.com/inward/record.url?scp=37049074200&partnerID=8YFLogxK

U2 - 10.1039/p19940000477

DO - 10.1039/p19940000477

M3 - Journal article

AN - SCOPUS:37049074200

SN - 1472-7781

SP - 477

EP - 481

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 4

ER -

Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman

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