Total synthesis of zyzzyanones A-D

被引：15

作者：

Nadkarni, Dwayaja H. ^{[1
]}

Murugesan, Srinivasan ^{[1
]}

Velu, Sadanandan E. ^{[1
]}

机构：

[1] Univ Alabama Birmingham, Dept Chem, Birmingham, AL 35294 USA

来源：

TETRAHEDRON | 2013年 / 69卷 / 20期

关键词：

Zyzzyanone; Marine; Alkaloid; Quinone; Mn(OAc)(3); MARINE NATURAL-PRODUCTS; FREE-RADICAL REACTIONS; CYTOTOXIC PYRROLOIMINOQUINONES; SPONGE; ALKALOIDS; DISCORHABDIN; DEEP; MAKALUVAMINES; ANALOGS; DRUGS;

D O I：

10.1016/j.tet.2013.03.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4105 / 4113

页数：9

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