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

MPS-Authors
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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Radkowski,  Karin
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Grabowski,  Jaroslaw
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wirtz,  Cornelia
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mynott,  Richard
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Radkowski, K., Grabowski, J., Wirtz, C., & Mynott, R. (2000). Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone. The Journal of Organic Chemistry, 65(25), 8758-8762. doi:10.1021/jo0012952.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-4873-3
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 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.