Studies on the synthesis of akuammiline alkaloids.: Access to 3,4-secoakuammilan derivatives

被引：21

作者：

Bennasar, ML ^{[1
]}

Zulaica, E ^{[1
]}

Ramírez, A ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(99)00070-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cleavage of the C-3/N-4 Pond of tetracycles 1 and 6 with chloroformates or acyl chlorides, followed by reduction, led to tetrahydrocarbazoles 4a,b and 8b-d, from which dithioacetal 12 and sulfoxides 5a,b, 11, and 17 were prepared. Whereas attempts to construct the quaternary C-7 centre of akuammiline alkaloids either by DMTSF-promoted cyclization of 12 or by Pummerer cyclization of sulfoxides 5a,b and 11 resulted in failure, sulfoxide 17 underwent cyclization on the indole 3-position to give the tetracyclic 3,4-secoakuammilan-type derivative 18. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3117 / 3128

页数：12

共 24 条

[1]

ALVAREZ M, 1994, CHEM HETEROCYCLI 4 S, V25, P248

[2] 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

[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]

[Anonymous], CHEM HETEROCYCLIC CO

[5]

Bennasar ML, 1996, HETEROCYCLES, V43, P1959

[6] Synthetic efforts toward akuammiline alkaloids from tetracyclic 6,7-seco derivatives [J].

Bennasar, ML ;

Zulaica, E ;

Ramirez, A ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1239-1251

[7] Construction of the quaternary C-7 centre of akuammiline alkaloids. Synthesis of 3,4-secoakuammilan derivatives [J].

Bennasar, ML ;

Zulaica, E ;

Ramirez, A ;

Bosch, J .

TETRAHEDRON LETTERS, 1996, 37 (36) :6611-6614

[8]

CALVERLEY MJ, 1983, J CHEM RES-S, P1848

[9] SYNTHESIS OF THE AZIRIDINO[1,2-A]PYRROLIDINE SUBSTRUCTURE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B [J].

COLEMAN, RS ;

CARPENTER, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5813-5815

[10] SYNTHESIS OF TETRAHYDROISOQUINOLINES VIA INTRAMOLECULAR ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS OF PUMMERER-DERIVED SUBSTITUTED N-BENZYL-N-TOSYL-ALPHA-AMINOTHIONIUM IONS [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON, 1992, 48 (37) :7803-7816

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