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

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