Total synthesis of (+)-papuamine: An antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp.

被引：37

作者：

Barrett, AGM ^{[1
]}

Boys, ML ^{[1
]}

Boehm, TL ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期

关键词：

D O I：

10.1021/jo951413z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+)-papuamine, the antipode of the C-2-symmetric, optically active, pentacyclic diamine natural product, starting from a chiral diol is described. The diol is available via an asymmetric Diels-Alder reaction between 1,3-butadiene and di-(-)-menthyl fumarate. The key transformation in the synthesis is sin intramolecular Pd(0)-catalyzed (Stille) coupling reaction to form the central 13-membered diazadiene macrocyclic ring.

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页码：685 / 699

页数：15

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