Formal total syntheses of crocacin A-D

被引：18

作者：

Besev, M ^{[1
]}

Brehm, C ^{[1
]}

Fürstner, A ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2005年 / 70卷 / 10期

关键词：

aldol reaction; alkyne; cross-coupling reactions; natural product synthesis; palladium; polyketides;

D O I：

10.1135/cccc20051696

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise route to the common polyketide fragment 5 of crocacin A -D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features a syn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzed anti-selective addition of propargyl mesylate 10 to the chiral aldehyde 9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

引用

页码：1696 / 1708

页数：13

共 46 条

[1]

Boeckman R.K., 2000, J ORG SYN, V77, P141, DOI 10.15227/orgsyn.077.0141

[2]

BREHM C, UNPUB

[3] Total synthesis of (+)-crocacin A [J].