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DOI: 10.1055/s-0029-1217974
Total Synthesis of (+)-Aspicilin from d-Mannitol
Publikationsverlauf
Publikationsdatum:
09. September 2009 (online)
Abstract
The total synthesis of the 18-membered lichen macrolide, (+)-aspicilin, has been accomplished utilizing the Swern oxidation, Masamune-Roush olefination, and ring-closing metathesis of a trienic ester as key steps. d-Mannitol has been utilized as the chiral pool material for the construction of the olefinic aldehyde and the Jacobsen hydrolytic kinetic resolution has been employed for the construction of the olefinic phosphonate ester.
Key words
(+)-aspicilin - Swern - Masamune-Roush olefination - ring-closing metathesis - d-mannitol - kinetic resolution
- Supporting Information for this article is available online:
- Supporting Information (PDF)
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References and Notes
Experimental procedures and spectral data for selected compounds are given in the Supporting Information.