Protecting group directed ring-closing metathesis (RCM): the first total synthesis of an anti-malarial nonenolide

被引：69

作者：

Mohapatra, Debendra K. ^{[1
]}

Ramesh, Dhondi K.

Giardello, Michael A.

Chorghade, Mukund S.

Gurjar, Mukund K.

Grubbs, Robert H.

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mable Beckman Labs Chem Synth, Pasadena, CA 91125 USA

[2] Materia Inc, Pasadena, CA 91107 USA

[3] Natl Chem Lab, Divv Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 14期

关键词：

nonenolide; anti-malarial agent; 1,2-O-isopropylidene; D-glyceraldehyde; Yamaguchi esterification; ring-closing metathesis;

D O I：

10.1016/j.tetlet.2007.02.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of a newly found naturally occurring anti-malarial nonenolide is described. A pivotal step in the synthesis is the ring-closing metathesis of a dienoic ester prepared by coupling an acid and alcohol that were stereoselectively synthesized from (S)-alpha-hydroxy-gamma-butyrolactone and 1,2-O-isopropylidene D-glyceraldchyde, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2621 / 2625

页数：5

共 53 条

[1]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[2] Formation of medium-size bridged ring systems via ring-closing metathesis of 2,5-disubstituted-2,3-dihydro-1H-pyrroles [J].