Synthesis of (2S, 3S)-β-methyltryptophan

Guoxia Han; Arwel Lewis; Victor J. Hruby

doi:10.1016/S0040-4039(01)00718-3

Synthesis of (2S, 3S)-β-methyltryptophan

Guoxia Han, Arwel Lewis, Victor J. Hruby

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

30 Scopus citations

Abstract

N^α-Fmoc-protected (2S, 3S)-β-methyltryptophan has been synthesized by asymmetric synthesis through the aid of an oxazolidinone auxiliary. Coupling of the mixed anhydride of Nⁱⁿ-Boc-protected indoleacrylic acid to the oxazolidinone auxiliary was achieved by lithium bromide and N, N-dimethylpyridine (DMAP). This reaction is milder and more convenient to run than the traditional conditions using butyl lithium.

Original language	English (US)
Pages (from-to)	4601-4603
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4039(01)00718-3
State	Published - Jul 9 2001
Externally published	Yes

Keywords

Auxiliary assisted asymmetric synthesis
Constrained amino acids
Lithium bromide (LiBr)
N, N-dimethylaminopyridine (DMAP)
β-methyltryptophan

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00718-3

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title = "Synthesis of (2S, 3S)-β-methyltryptophan",

abstract = "Nα-Fmoc-protected (2S, 3S)-β-methyltryptophan has been synthesized by asymmetric synthesis through the aid of an oxazolidinone auxiliary. Coupling of the mixed anhydride of Nin-Boc-protected indoleacrylic acid to the oxazolidinone auxiliary was achieved by lithium bromide and N, N-dimethylpyridine (DMAP). This reaction is milder and more convenient to run than the traditional conditions using butyl lithium.",

keywords = "Auxiliary assisted asymmetric synthesis, Constrained amino acids, Lithium bromide (LiBr), N, N-dimethylaminopyridine (DMAP), β-methyltryptophan",

author = "Guoxia Han and Arwel Lewis and Hruby, {Victor J.}",

year = "2001",

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day = "9",

doi = "10.1016/S0040-4039(01)00718-3",

language = "English (US)",

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pages = "4601--4603",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of (2S, 3S)-β-methyltryptophan

AU - Han, Guoxia

AU - Lewis, Arwel

AU - Hruby, Victor J.

PY - 2001/7/9

Y1 - 2001/7/9

N2 - Nα-Fmoc-protected (2S, 3S)-β-methyltryptophan has been synthesized by asymmetric synthesis through the aid of an oxazolidinone auxiliary. Coupling of the mixed anhydride of Nin-Boc-protected indoleacrylic acid to the oxazolidinone auxiliary was achieved by lithium bromide and N, N-dimethylpyridine (DMAP). This reaction is milder and more convenient to run than the traditional conditions using butyl lithium.

AB - Nα-Fmoc-protected (2S, 3S)-β-methyltryptophan has been synthesized by asymmetric synthesis through the aid of an oxazolidinone auxiliary. Coupling of the mixed anhydride of Nin-Boc-protected indoleacrylic acid to the oxazolidinone auxiliary was achieved by lithium bromide and N, N-dimethylpyridine (DMAP). This reaction is milder and more convenient to run than the traditional conditions using butyl lithium.

KW - Auxiliary assisted asymmetric synthesis

KW - Constrained amino acids

KW - Lithium bromide (LiBr)

KW - N, N-dimethylaminopyridine (DMAP)

KW - β-methyltryptophan

UR - http://www.scopus.com/inward/record.url?scp=0035833077&partnerID=8YFLogxK

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U2 - 10.1016/S0040-4039(01)00718-3

DO - 10.1016/S0040-4039(01)00718-3

M3 - Article

AN - SCOPUS:0035833077

SN - 0040-4039

VL - 42

SP - 4601

EP - 4603

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

Synthesis of (2S, 3S)-β-methyltryptophan

Abstract

Keywords

ASJC Scopus subject areas

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