A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate

被引：25

作者：

Emmanuvel, Lourdusamy ^{[1
]}

Sudalai, Arumugam ^{[1
]}

机构：

[1] Natl Chem Lab, Chem Engn & Proc Dev Div, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 40期

关键词：

1,2-aminoalcohols; asymmetric epoxidation; 3,3-sigmatropic rearrangement; lactone;

D O I：

10.1016/j.tetlet.2008.07.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a delta-azidolactone was used in the construction of the piperidine moiety. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5736 / 5738

页数：3

共 32 条

[1] An epoxidation approach to a chiral lactone: Application of the Shi epoxidation [J].

Ager, David J. ;

Anderson, Ken ;

Oblinger, Eric ;

Shi, Yian ;

VanderRoest, James .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :44-51

[2]

[Anonymous], LETT DRUG DES DISCOV

[3]

[Anonymous], J PHYSL

[4]

Baker R., 1993, Eur. Patent, Patent No. [528495, 0528495A1, 0528495]

[5] Stereoselective synthesis of L-733,060 [J].

Bhaskar, G ;

Rao, BV .

TETRAHEDRON LETTERS, 2003, 44 (05) :915-917

[6]

CHANG MM, 1970, J BIOL CHEM, V245, P4784

[7] Substance P: Structure, function, and therapeutics [J].

Datar, P ;

Srivastava, S ;

Coutinho, E ;

Govil, G .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2004, 4 (01) :75-103

[8] α-Amino 1,3-dithioketal mediated asymmetric synthesis of piperidines (L-733,060) and tetrahydrofuran glycines [J].

Davis, Franklin A. ;

Ramachandar, Tokala .

TETRAHEDRON LETTERS, 2008, 49 (05) :870-872

[9] DISCOVERY OF A POTENT SUBSTANCE-P ANTAGONIST - RECOGNITION OF THE KEY MOLECULAR DETERMINANT [J].

DESAI, MC ;

LEFKOWITZ, SL ;

THADEIO, PF ;

LONGO, KP ;

SNIDER, RM .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (26) :4911-4913

[10] PIPERIDINE-ETHER BASED HNK(1) ANTAGONISTS .1. DETERMINATION OF THE RELATIVE AND ABSOLUTE STEREOCHEMICAL REQUIREMENTS [J].

HARRISON, T ;

WILLIAMS, BJ ;

SWAIN, CJ ;

BALL, RG .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) :2545-2550

← 1 2 3 4 →