Abnormal Pummerer cyclizations on the indole ring

被引：14

作者：

Amat, M ^{[1
]}

Bennasar, ML ^{[1
]}

Hadida, S ^{[1
]}

Sufi, BA ^{[1
]}

Zulaica, E ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 29期

关键词：

D O I：

10.1016/0040-4039(96)01030-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfides 2 and 7 are formed from sulfoxides 1 and 4a, respectively, under Pummerer reaction conditions. The process involves the formation of a positively charged seven-membered ring intermediate by nucleophilic attack of the indole nucleus on the initially formed acyloxysulfonium sail. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5217 / 5220

页数：4

共 15 条

[1] STUDIES ON THE SYNTHESIS OF PENTACYCLIC STRYCHNOS INDOLE ALKALOIDS - CLOSURE OF E-RING BY PUMMERER CYCLIZATION [J].

AMAT, M ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5792-5796

[2] A new synthetic entry to the indolo[2,3-a]quinolizidine system. Electrophilic cyclizations on the indole ring from 2-(2-piperidyl)indoles [J].

Amat, M ;

Hadida, S ;

Sathyanarayana, S ;

Bosch, J .

TETRAHEDRON LETTERS, 1996, 37 (17) :3071-3074

[3] A NEW SYNTHETIC ENTRY TO PENTACYCLIC STRYCHNOS ALKALOIDS - TOTAL SYNTHESIS OF (+/-)-TUBIFOLIDINE, (+/-)-TUBIFOLINE, AND (+/-)-19,20-DIHYDROAKUAMMICINE [J].

AMAT, M ;

LINARES, A ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6299-6312

[4] STUDIES ON THE SYNTHESIS OF MAVACURINE-TYPE INDOLE ALKALOIDS - 1ST TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-2,7-DIHYDROPLEIOCARPAMINE [J].

BENNASAR, ML ;

ZULAICA, E ;

JIMENEZ, JM ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7756-7767

[5]

BENNASAR ML, IN PRESS J TETRAHEDR

[6] METHODS FOR INDOLE ALKALOID SYNTHESIS - A STUDY OF THE COMPATIBILITY OF THE INDOLE 2,3-QUINODIMETHANE STRATEGY FOR THE SYNTHESIS OF 16-METHOXY-SUBSTITUTED ASPIDOSPERMA-TYPE ALKALOIDS - SYNTHESIS OF (+)- AND (-)-16-METHOXYTABERSONINE [J].

CARDWELL, K ;

HEWITT, B ;

LADLOW, M ;

MAGNUS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2242-2248

[7] THE PUMMERER CYCLIZATION ROUTE TO THE IBOPHYLLIDINE ALKALOIDS - TOTAL SYNTHESIS OF (+/-)-DEETHYLIBOPHYLLIDINE [J].

CATENA, J ;

VALLS, N ;

BOSCH, J ;

BONJOCH, J .

TETRAHEDRON LETTERS, 1994, 35 (25) :4433-4436

[8]

De Lucchi O., 1991, ORG REACTIONS, V40, P157, DOI DOI 10.1002/0471264180.0R040.03

[9] PENTACYCLIC SYSTEMS FOR INDOLE ALKALOIDS - FORMATION OF THE C-11-C-12 BOND - 2 SYNTHESES OF (/-)-ASPIDOSPERMIDINE [J].

GALLAGHER, T ;

MAGNUS, P ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4750-4757

[10]

GRIERSON DS, 1991, COMPREHENSIVE ORGANI, V6, pCH47

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