Modification of the butenyl-spinosyns utilizing cross-metathesis

被引：19

作者：

Daeuble, John ^{[1
]}

Sparks, Thomas C. ^{[1
]}

Johnson, Peter ^{[1
]}

Graupner, Paul R. ^{[1
]}

机构：

[1] Dow AgroSci, Indianapolis, IN 46268 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 12期

关键词：

Spinosyns; Natural Products; Semi-synthesis; Olefin cross-metathesis; RING-CLOSING METATHESIS; ACRYLONITRILE; DERIVATIVES; CHEMISTRY; COMPLEX;

D O I：

10.1016/j.bmc.2009.02.036

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The discovery of a strain of Saccharopolyspora sp. that produced a number of spinosyn analogs that had not before been seen gave an ideal opportunity for extending our knowledge of that SAR of these highly efficacious insecticides. In particular, these compounds contained a butenyl group connected to C-21 which in the regular spinosyns was substituted with a simple ethyl group. The double bond therefore gave us a handle to further modify this position allowing us to substitute different groups there. In this paper we show one of our approaches to this modi. cation using olefin cross-metathesis. Even though the spinosyns were not highly efficient substrates for metathesis reactions, we were nevertheless successful in extending their chemistry accordingly. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4197 / 4205

页数：9

共 28 条

[1] A general model for selectivity in olefin cross metathesis [J].