Modular Total Synthesis of Rhizopodin: A Highly Potent G-Actin Dimerizing Macrolide

被引：36

作者：

Kretschmer, Manuel ^{[1
]}

Dieckmann, Michael ^{[2
]}

Li, Pengfei ^{[1
]}

Rudolph, Sven ^{[1
]}

Herkommer, Daniel ^{[2
]}

Troendlin, Johannes ^{[1
]}

Menche, Dirk ^{[2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 47期

关键词：

macrocycles; natural products; polyketides; rhizopodin; total synthesis; MYXOCOCCUS-STIPITATUS MYXOBACTERIA; ASYMMETRIC TRANSFER HYDROGENATION; ANTI-MARKOVNIKOV HYDRATION; WADSWORTH-EMMONS REACTION; MEDIATED ALDOL REACTION; N-ACYL OXAZOLIDINONES; BETA-HYDROXY KETONES; STEREOSELECTIVE-SYNTHESIS; CARBOXYLIC ESTERS; MARINE MACROLIDES;

D O I：

10.1002/chem.201302197

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29steps by employing a concise strategy that exploits the molecules C-2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site-directed sequential cross-coupling strategy and the bidirectional attachment of the side chains by means of Horner-Wadsworth-Emmons (HWE) coupling reactions. During the course of this endeavor, scalable routes for synthesis of three main building blocks of similar complexity were developed that allowed for their stereocontrolled construction. This modular route will be amenable to the development of syntheses of other analogues of rhizopodin.

引用

页码：15993 / 16018

页数：26

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