PMID: 11112600Jan 11, 2000

Ring-closing alkyne metathesis. Application to the total synthesis of sophorolipid lactone

The Journal of Organic Chemistry
A FürstnerRichard Mynott

Abstract

The first total synthesis of a major component of the microbial biosurfactant sophorolipid has been achieved. This approach to the 26-membered macrolide 1 containing a Z-configured alkene group in its lipidic tether spanning the sophorose backbone is based on a ring-closing metathesis reaction of diyne 21 catalyzed by Mo[N(t-Bu)(Ar)](3) (5; Ar = 3,5-dimethylphenyl) activated in situ by CH(2)Cl(2), followed by Lindlar reduction of the resulting cycloalkyne 22. The two beta-glycosidic linkages of compound 21 were installed by means of the glucal epoxide method and a modified Koenigs-Knorr reaction promoted by AgOTf/lutidine, respectively.

Citations

May 6, 2003·Bioorganic & Medicinal Chemistry Letters·Jean-Bernard BehrGeorges Guillerm
May 7, 2005·Chemical Communications : Chem Comm·Alois Fürstner, Paul W Davies
May 27, 2005·Proceedings of the National Academy of Sciences of the United States of America·Alois FürstnerOliver Müller
Oct 20, 2005·Journal of Bioscience and Bioengineering·Dai KitamotoTadaatsu Nakahara
May 15, 2015·Letters in Applied Microbiology·A Varvaresou, K Iakovou
Mar 23, 2017·Organic Letters·Santanu JanaSuvarn S Kulkarni
Sep 19, 2016·Carbohydrate Research·Debjani Si, Mark W Peczuh
Jun 1, 2016·Angewandte Chemie·Lifeng SunXin-Shan Ye
Jan 21, 2017·Carbohydrate Research·Takashi MoriyaTadao Saito
Dec 19, 2014·Chemistry : a European Journal·Gaëlle ValotAlois Fürstner
Oct 13, 2011·Angewandte Chemie·Konrad LehrAlois Fürstner
Oct 23, 2018·Chemistry : a European Journal·Henrike Ehrhorn, Matthias Tamm
Sep 5, 2007·Chemistry : a European Journal·Alois FürstnerRichard Mynott
Nov 2, 2007·Angewandte Chemie·Alois FürstnerLudovic Jean
Apr 22, 2005·Angewandte Chemie·Alois Fürstner, Laurent Turet
Feb 26, 2009·Chemistry : a European Journal·Alois FürstnerJun'ichi Kobayashi
Aug 22, 2009·Chemistry : a European Journal·Takashi NaganoAlois Fürstner
Jul 9, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Oct 1, 2005·Chemistry : a European Journal·Alois Fürstner, Margarita Wuchrer
Dec 16, 2005·Angewandte Chemie·Haim WeissmanJeffrey S Moore
Nov 9, 2006·Chemistry : a European Journal·Alois FürstnerChristian W Lehmann
Oct 13, 2009·Chemistry : a European Journal·Martin BindlAlois Fürstner
Apr 17, 2013·Chemistry : a European Journal·Azusa KondohAlois Fürstner
Oct 3, 2002·Chemical Communications : Chem Comm·Alois Fürstner, Karin Radkowski
Jul 28, 2011·Angewandte Chemie·Stefan BensonAlois Fürstner
Jan 29, 2013·Angewandte Chemie·Alois Fürstner
Feb 2, 2002·Chemistry : a European Journal·A FürstnerG Blanda
Jan 22, 2005·Angewandte Chemie·Xiaowu Yang, Bing Gong

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