Asymmetric synthesis of (-)-(R)-pyrrolam A starting from (S)-malic acid

被引：42

作者：

Huang, PQ ^{[1
]}

Chen, QF ^{[1
]}

Chen, CL ^{[1
]}

Zhang, HK ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(99)00395-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An asymmetric synthesis of natural (-)-pyrrolam A starting from natural (S)-malic acid is described. The stereogenic center was established via a highly trans-diastereoselective reductive alkylation procedure. A tandem base-induced intramolecular amide N-substitution and tosic acid elimination led to the target molecule. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3827 / 3832

页数：6

共 24 条

[1] First total synthesis of pyrrolam A [J].

Aoyagi, Y ;

Manabe, T ;

Ohta, A ;

Kurihara, T ;

Pang, GL ;

Yuhara, T .

TETRAHEDRON, 1996, 52 (03) :869-876

[2]

BEAK P, 1986, ACCOUNTS CHEM RES, V19, P3187

[3] STEREOSELECTIVE SYNTHESIS OF STATIN ANALOGS [J].

BERNARDI, A ;

MICHELI, F ;

POTENZA, D ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (34) :4949-4952

[4] A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662

[5] The preparation of benzyloxyalkyl p-toluenesulfonates [J].

Butler, CL ;

Renfrew, AG ;

Clapp, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :1472-1473

[6]

DAI WM, 1990, HETEROCYCLES, V30, P1231

[7]

GROTE R, 1990, LIEBIGS ANN CHEM, P525

[8] N-ACYLIMINIUM ION REARRANGEMENTS - GENERALITIES AND APPLICATION TO THE SYNTHESIS OF PYRROLIZIDINE ALKALOIDS [J].

HART, DJ ;

YANG, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :235-242

[9] A versatile approach to the activated form of (3S, 4R)-statine and its analogues [J].

Huang, PQ ;

Ye, JL ;

Chen, Z ;

Ruan, YP ;

Gao, JX .

SYNTHETIC COMMUNICATIONS, 1998, 28 (03) :417-426

[10] First asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation [J].

Huang, PQ ;

Wang, SL ;

Zheng, H ;

Fei, XS .

TETRAHEDRON LETTERS, 1997, 38 (02) :271-272

← 1 2 3 →