Synthesis of enantiopure (2R,3aS,7aS)-2-ethyloctahydroindol-6-one and its Fischer indolization

被引：16

作者：

Bonjoch, J

Catena, J

Terricabras, D

Fernandez, JC

LopezCanet, M

Valls, N

机构：

[1] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 18期

关键词：

D O I：

10.1016/S0957-4166(97)00379-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A diastereoselective synthesis of (-)-2-ethyloctahydroindol-6-one 12 starting from O-methyl-L-tyrosine 1 is described. The process first involves the synthesis of enantiopure (-)-1-(4-methoxyphenyl)-2-butylamine 8, which, after Birch reduction, N-benzylation and acid treatment, renders the cis-fused azabicyclo 12. Studies on the Fischer indolization of 12 are also reported. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3143 / 3151

页数：9

相关论文

共 27 条

[1]

BALL JB, 1987, HETEROCYCLES, V26, P1573

[2]

BAN Y, 1969, TETRAHEDRON LETT, P2523

[3] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .13. THE FISCHER INDOLIZATION OF 2-AZABICYCLO[3.3.1]NONAN-7-ONES - A NEW ENTRY TO THE DASYCARPIDAN RING-SYSTEM [J].

BONJOCH, J ;

CASAMITJANA, N ;

GRACIA, J ;

UBEDA, MC ;

BOSCH, J .

TETRAHEDRON LETTERS, 1990, 31 (17) :2449-2452

[4] Synthesis of the octahydroindole core of aeruginosins: A new bicyclic alpha-amino acid [J].

Bonjoch, J ;

Catena, J ;

Isabal, E ;

LopezCanet, M ;

Valls, N .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1899-1902

[5] Total synthesis of (+/-)-deethylibophyllidine: Studies of a Fischer indolization route and a successful approach via a pummerer rearrangement/thionium ion-mediated indole cyclization [J].

Bonjoch, J ;

Catena, J ;

Valls, N .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7106-7115

[6] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - CHIRALLY SPECIFIC SYNTHESES OF TYLOPHORINE AND CRYPTOPLEURINE [J].

BUCKLEY, TF ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4222-4232

[7] Solid phase synthesis of spiroindoline [J].

Cheng, Y ;

Chapman, KT .

TETRAHEDRON LETTERS, 1997, 38 (09) :1497-1500

[8]

Coppola G.M., 1987, ASYMMETRIC SYNTHESIS

[9] A STRAIGHTFORWARD ROUTE TO IBOPHYLLIDINE ALKALOIDS BY A DOUBLE TRANSANNULAR CYCLIZATION [J].

FERNANDEZ, JC ;

VALLS, N ;

BOSCH, J ;

BONJOCH, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (22) :2317-2318

[10] FISCHER INDOLE SYNTHESIS FROM CIS AND TRANS-HEXAHYDRO-7-METHYL-6-ISOQUINOLONES - H-1-NMR DETERMINATION OF THE CONFIGURATION AND CONFORMATION OF PRODUCTS [J].

FRETER, K ;

FUCHS, V ;

PITNER, TP .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4593-4597