Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon

被引：95

作者：

Huang, PQ ^{[1
]}

Liu, LX ^{[1
]}

Wei, BG ^{[1
]}

Ruan, YP ^{[1
]}

机构：

[1] Xiamen Univ, Dept Chem, Fujian 361005, Peoples R China

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 11期

关键词：

D O I：

10.1021/ol034505g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Selective and potent neurokinin substance P receptor antagonists (+)-L-733, 060 (1) and (+)-CP-99, 994 (2) have been synthesized starting from a new (3S)-piperidinol synthon derived from L-glutamic acid. The methods featured a C-2 regioselective reduction of glutarimide (9), Lewis acid-promoted Si to C-2 phenyl group migration of 10, and stereoselective reduction of acetylated oxime 19 as the key steps.

引用

页码：1927 / 1929

页数：3

共 30 条

[1]

Baker R, European Patent, Patent No. [EP0528495A1, 0528495]

[2]

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

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

Bhaskar, G ;

Rao, BV .

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

[4] Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidines, precursors of non-peptidic substance P antagonists [J].

Calvez, O ;

Langlois, N .

TETRAHEDRON LETTERS, 1999, 40 (39) :7099-7100

[5] Stereoselective synthesis of (+)-CP-99,994: A substance P non-peptide antagonist. [J].

Chandrasekhar, S ;

Mohanty, PK .

TETRAHEDRON LETTERS, 1999, 40 (27) :5071-5072

[6] SYNTHESIS OF (+/-)-CP-99,994 - A HIGHLY POTENT SUBSTANCE-P ANTAGONIST [J].

DESAI, MC ;

THADEIO, PF ;

LEFKOWITZ, SL .

TETRAHEDRON LETTERS, 1993, 34 (37) :5831-5834

[7] 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

[8]

Gringore OR, 1990, ORG SYNTH COLL, V7, P99

[9] 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

[10] A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues [J].

Huang, PQ ;

Zheng, XA ;

Wang, SL ;

Ye, JL ;

Jin, LR ;

Chen, Z .

TETRAHEDRON-ASYMMETRY, 1999, 10 (17) :3309-3317

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