Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone

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 di...

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Published inJournal of organic chemistry Vol. 65; no. 25; pp. 8758 - 8762
Main Authors Fürstner, Alois, Radkowski, Karin, Grabowski, Jaroslaw, Wirtz, Conny, Mynott, Richard
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TORULOPSIS-BOMBICOLA
BIOSURFACTANT
CANDIDA-BOMBICOLA
RESIN GLYCOSIDES
OLIGOSACCHARIDES
3-COORDINATE MOLYBDENUM(III)
KINETIC RESOLUTION
CONVENIENT PREPARATION
OLEFIN METATHESIS
MICROBIAL-PRODUCTION
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Summary: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 CH2Cl2, followed by Lindlar reduction of the resulting cycloalkyne 22. The two β-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.
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ark:/67375/TPS-V8JVQZQZ-9
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo0012952