Application of allylic substitutions in natural products synthesis

Author:

Helmchen G.1,Ernst Martin1,Paradies G.1

Affiliation:

1. 1Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany

Abstract

Synthesis routes are described, allowing all known jasmonoids as well as their enantiomers to be synthesized in enantiomerically and diastereomerically pure form. The routes are based on a set of closely related lactones containing an electrophilic allylic moiety, which are accessible via asymmetric Pd-catalyzed allylic alkylation. Regio- and diastereoselective SN2'-anti-reactions of the electrophilic lactones with organocopper compounds furnished 2,3-cis-disubstituted cyclopentenones, which were further transformed into the target compounds, i.e., 12-oxophytodienoic acid (12-OPDA) in excellent overall yields. The methodology also allowed iridoids and isoprostanes to be prepared. The configuration of an Archaea membrane lipid constituent containing cyclopentane rings was determined by total synthesis of a diol that was also obtained by degradation of the natural product.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Reference3 articles.

1. had previously been prepared from the chiral pool of sugar compounds a Synthesis;Lactone;Chem Soc Trans,1999

2. a and Application of allylic substitutions in natural products synthesis in of Extreme Environments and its Potential for Biotechnology da Amsterdam a;Eguchi;Org Chem Phytochemistry Phytochemistry Pure Applied Chemistry Phytochemistry review Microbiology Lipid Res Helv Chim Acta Helv Chim Acta Helv Chim Acta Org Chem,1997

3. cited therein a a a;Grieco;Org Chem Matsuumi Tetrahedron Lett Chem Soc Chem Commun Chem Soc Trans Tetrahedron Lett Eur Org Chem,1989

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3