A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

Sébastien Prévost; Phannarath Phansavath; Mansour Haddad

doi:10.1016/j.tetasy.2009.12.010

A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

Sébastien Prévost
, Phannarath Phansavath
, Mansour Haddad

PSL University

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

Abstract

An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.

Original language	English
Pages (from-to)	16-20
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	1
DOIs	https://doi.org/10.1016/j.tetasy.2009.12.010
Publication status	Published - 29 Jan 2010
Externally published	Yes

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title = "A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate",

abstract = "An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.",

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AU - Prévost, Sébastien

AU - Phansavath, Phannarath

AU - Haddad, Mansour

PY - 2010/1/29

Y1 - 2010/1/29

N2 - An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.

AB - An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.

U2 - 10.1016/j.tetasy.2009.12.010

DO - 10.1016/j.tetasy.2009.12.010

M3 - Article

AN - SCOPUS:76049112828

SN - 0957-4166

VL - 21

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 1

ER -

A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

Abstract

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