Synthesis of cleayamine-type indole alkaloids and their 5-nor derivatives by a ring-closing metathesis-vinyl halide Heck cyclization strategy

被引：12

作者：

Bennasar, M. -Lluisa ^{[1
,2
]}

Sole, Daniel ^{[1
,2
]}

Zulaica, Ester ^{[1
,2
]}

Alonso, Sandra ^{[1
,2
]}

机构：

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

[2] Univ Barcelona, Inst Biomed IBUB, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2013年 / 69卷 / 12期

关键词：

Alkaloids; Cleavamines; Ring-closing metathesis; Heck cyclization; MEDIUM-SIZED RINGS; STEREOCONTROLLED SYNTHESIS; STRYCHNOS ALKALOIDS; NORFLUOROCURARINE; (-)-STRYCHNINE; CONSTRUCTION; HETEROCYCLES; ERVITSINE; ACCESS; CORE;

D O I：

10.1016/j.tet.2013.01.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An indole-templated RCM has been used to assemble the central medium-sized rings of the indole upper-half of vinorelbine and the cleavamine-type alkaloids. From these key intermediates, the bridged tetracyclic framework of the alkaloids is completed with the insertion of a 2-ethylpropeno unit, by N-alkylation followed by a challenging endocyclic vinyl halide Heck cyclization. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2534 / 2541

页数：8

共 3 条

[1] A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis-Vinyl Halide Heck Cyclization Strategy
Bennasar, M. -Lluisa
Sole, Daniel
Zulaica, Ester
Alonso, Sandra
[J]. ORGANIC LETTERS, 2011, 13 (08) : 2042 - 2045
[2] Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine
Bennasar, M-Lluisa
Zulaica, Ester
Sole, Daniel
Alonso, Sandra
[J]. TETRAHEDRON, 2012, 68 (24) : 4641 - 4648
[3] Synthesis of indole-based propellane derivatives via Weiss-Cook condensation, Fischer indole cyclization, and ring-closing metathesis as key steps
Kotha, Sambasivarao
Chinnam, Ajay Kumar
Tiwari, Arti
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2709 - 2714

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