Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

Wei Wang; Chiyi Xiong; Jianqing Yang; Victor J Hruby

doi:10.1016/S0040-4039(01)01626-4

Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

Wei Wang, Chiyi Xiong, Jianqing Yang, Victor J Hruby

Pharmacology and Toxicology

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of α-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D- and L-α-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.

Original language	English (US)
Pages (from-to)	7717-7719
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4039(01)01626-4
State	Published - Oct 29 2001

Keywords

Amino acids
Asymmetric hydrogenation
Suzuki cross coupling
Tryptophan

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01626-4

Cite this

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title = "Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives",

abstract = "An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of α-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D- and L-α-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.",

keywords = "Amino acids, Asymmetric hydrogenation, Suzuki cross coupling, Tryptophan",

author = "Wei Wang and Chiyi Xiong and Jianqing Yang and Hruby, {Victor J}",

note = "Funding Information: This work is supported by grants from the US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 06284). We thank Professor Dominic V. McGrath for using his group's polarimeter. The views expressed are those of the authors and not necessary those of the USPHS.",

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T1 - Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

AU - Wang, Wei

AU - Xiong, Chiyi

AU - Yang, Jianqing

AU - Hruby, Victor J

N1 - Funding Information: This work is supported by grants from the US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 06284). We thank Professor Dominic V. McGrath for using his group's polarimeter. The views expressed are those of the authors and not necessary those of the USPHS.

PY - 2001/10/29

Y1 - 2001/10/29

N2 - An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of α-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D- and L-α-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.

AB - An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of α-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D- and L-α-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.

KW - Amino acids

KW - Asymmetric hydrogenation

KW - Suzuki cross coupling

KW - Tryptophan

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

Abstract

Keywords

ASJC Scopus subject areas

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