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

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.

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[124]SI.pdf (Supplementary material), 814KB
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 Creators:
Fürstner, Alois1, Author           
Radkowski, Karin1, Author           
Grabowski, Jaroslaw1, Author           
Wirtz, Cornelia2, Author           
Mynott, Richard2, Author           
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              

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 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.

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Language(s): eng - English
 Dates: 2000-08-282000-11-102000-12-15
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo0012952
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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: 5 Volume / Issue: 65 (25) Sequence Number: - Start / End Page: 8758 - 8762 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1