Total Synthesis of (+)- Madangamine D

被引：37

作者：

Ballette, Roberto ^{[1
,2
]}

Perez, Maria ^{[1
,2
]}

Proto, Stefano ^{[1
,2
]}

Amat, Mercedes ^{[1
,2
]}

Bosch, Joan ^{[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：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 24期

关键词：

alkaloids; asymmetric synthesis; macrocycles; nitrogen heterocycles; total synthesis; SPONGE XESTOSPONGIA-INGENS; 1ST ENANTIOSELECTIVE SYNTHESIS; RACEMIC BICYCLIC LACTAMS; DIAZATRICYCLIC CORE; MARINE SPONGES; CIS-PERHYDROISOQUINOLINES; TRICYCLIC CORE; ALKALOIDS; CONSTRUCTION; ROUTE;

D O I：

10.1002/anie.201402263

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Madangamines are a group of bioactive marine sponge alkaloids, embodying an unprecedented diazapenta-cyclic skeletal type. The enantioselective total synthesis of madangamine D has been accomplished, and represents the first total synthesis of an alkaloid of the madangamine group. It involves the stereoselective construction of the diazatricyclic ABC core using a phenylglycinol-derived lactam as the starting enantiomeric scaffold and the subsequent assembly of the peripheral macrocyclic rings. The synthesis provides, for the first time, a pure sample of madangamine D and confirms the absolute configuration of this alkaloid family.

引用

页码：6202 / 6205

页数：4

共 35 条

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