DIMETHYL(METHYLTHIO)SULFONIUM FLUOROBORATE INDUCED CYCLIZATION OF DITHIOACETALS UPON 2,3-DISUBSTITUTED INDOLES

被引:23
作者
AMAT, M [1 ]
ALVAREZ, M [1 ]
BONJOCH, J [1 ]
CASAMITJANA, N [1 ]
GRACIA, J [1 ]
LAVILLA, R [1 ]
GARCIAS, X [1 ]
BOSCH, J [1 ]
机构
[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1016/S0040-4039(00)97420-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of dithioacetals 1a-c, 3, and 4 with DMTSF accomplishes cyclization upon the indole 3-position to give the Strychnos-type pentacles 2a-c, 10, and 11, respectively. © 1990.
引用
收藏
页码:3453 / 3456
页数:4
相关论文
共 22 条
[1]   SYNTHESIS AND NMR DATA OF THE STRYCHNOS INDOLE ALKALOID TUBIFOLINE [J].
AMAT, M ;
LINARES, A ;
MUNOZ, J ;
BOSCH, J .
TETRAHEDRON LETTERS, 1988, 29 (48) :6373-6376
[2]   1ST TOTAL SYNTHESIS AND NMR DATA OF THE STRYCHNOS ALKALOID 19,20-DIHYDROAKUAMMICINE [J].
AMAT, M ;
LINARES, A ;
BOSCH, J .
TETRAHEDRON LETTERS, 1989, 30 (17) :2293-2296
[3]   A NEW STRATEGY FOR THE SYNTHESIS OF PENTACYCLIC STRYCHNOS ALKALOIDS - SYNTHESIS OF (+/-)-TUBIFOLIDINE [J].
AMAT, M ;
LINARES, A ;
SALAS, ML ;
ALVAREZ, M ;
BOSCH, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (06) :420-421
[4]   GENERAL-METHOD FOR THE SYNTHESIS OF BRIDGED INDOLE ALKALOIDS - NUCLEOPHILIC-ADDITION OF INDOLEACETIC ESTER ENOLATES TO N-ALKYLPYRIDINIUM SALTS [J].
BENNASAR, ML ;
ALVAREZ, M ;
LAVILLA, R ;
ZULAICA, E ;
BOSCH, J .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1156-1168
[5]   AROMATIC ANNULATION WITH BISPHENYLTHIONIUM IONS [J].
BINMANAS, AR ;
SMITH, RAJ .
TETRAHEDRON, 1987, 43 (08) :1847-1856
[6]   STEREOCONTROLLED ACCESS TO DASYCARPIDAN-TYPE COMPOUNDS AND FORMAL TOTAL SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS OF THE STRYCHNAN-TYPE [J].
BONJOCH, J ;
CASAMITJANA, N ;
GRACIA, J ;
BOSCH, J .
TETRAHEDRON LETTERS, 1989, 30 (41) :5659-5662
[7]   A NEW SYNTHETIC ENTRY TO PENTACYCLIC STRYCHNOS INDOLE ALKALOIDS [J].
BOSCH, J ;
AMAT, M .
TETRAHEDRON LETTERS, 1985, 26 (40) :4951-4954
[8]   STUDIES ON THE SYNTHESIS OF PENTACYCLIC STRYCHNINOS INDOLE ALKALOIDS - PHOTOCYCLIZATION OF N-CHLOROACETYL-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANOAZOCINO[4,3-B] INDOLE-DERIVATIVES [J].
BOSCH, J ;
AMAT, M ;
SANFELIU, E .
TETRAHEDRON, 1985, 41 (12) :2557-2566
[9]  
Bosch J., 1988, STUDIES NATURAL PROD, VI, P31
[10]   THIOAMMONIUM IONS - AZASULFENYLATION REACTIONS [J].
CASERIO, MC ;
KIM, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3231-3233