（-）-5,6-二氢西奈霉素B的全合成
Total synthesis of (-)-5,6-dihydrocineromycin B.
作者信息
Li Guozhi, Yang Xiaoxia, Zhai Hongbin
机构信息
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
出版信息
J Org Chem. 2009 Feb 6;74(3):1356-9. doi: 10.1021/jo802503x.
PMID:19115810
Abstract
An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.
摘要
已从（-）-芳樟醇O-三乙基甲硅烷基醚经13步或从香叶醇经12步完成了（-）-5,6-二氢cinermycin B的不对称全合成。本合成的特点是：（i）涉及具有酮膦酸酯官能团的醛的分子间维蒂希反应，以及（ii）分子内霍纳-沃兹沃思-埃蒙斯烯化反应。
相似文献
1
Total synthesis of (-)-5,6-dihydrocineromycin B.
J Org Chem. 2009 Feb 6;74(3):1356-9. doi: 10.1021/jo802503x.
2
A total synthesis of the antitumour macrolide rhizoxin D.
Org Biomol Chem. 2005 Dec 21;3(24):4412-31. doi: 10.1039/b507570j. Epub 2005 Nov 15.
3
The total synthesis of (+)-migrastatin.
J Am Chem Soc. 2003 May 21;125(20):6042-3. doi: 10.1021/ja0349103.
4
Synthesis of gamma,delta-unsaturated-beta-keto lactones via sequential cross metathesis-lactonization: a facile entry to macrolide antibiotic (-)-A26771B.
J Org Chem. 2006 Mar 3;71(5):2021-5. doi: 10.1021/jo052421a.
5
Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization.
Org Lett. 2013 Jun 21;15(12):2998-3001. doi: 10.1021/ol401186f. Epub 2013 Jun 3.
6
Formal total synthesis of the polyketide macrolactone narbonolide.
J Org Chem. 2005 Sep 2;70(18):7267-72. doi: 10.1021/jo050924a.
7
Enantioselective total synthesis of (+)-neosymbioimine.
Org Lett. 2007 Apr 12;9(8):1461-4. doi: 10.1021/ol070049a. Epub 2007 Mar 23.
8
An efficient and stereoselective synthesis of the monomeric counterpart of marinomycin A.
Org Lett. 2007 Apr 12;9(8):1453-6. doi: 10.1021/ol070240k. Epub 2007 Mar 14.
9
Synthesis of sporiolide B from D-glucal.
Carbohydr Res. 2007 Aug 13;342(11):1405-11. doi: 10.1016/j.carres.2007.04.013. Epub 2007 Apr 29.
10
Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach.
Org Lett. 2005 May 26;7(11):2261-4. doi: 10.1021/ol0507625.
Zotero 插件