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Synthesis 2017; 49(07): 1702-1706
DOI: 10.1055/s-0036-1589471
DOI: 10.1055/s-0036-1589471
paper
Stereoselective Total Synthesis of (S)-Stigmolone: A Fruiting-Body-Inducing Pheromone
Weitere Informationen
Publikationsverlauf
Received: 22. September 2016
Accepted after revision: 04. November 2016
Publikationsdatum:
14. Dezember 2016 (online)
Abstract
The total synthesis of (S)-stigmolone, a pheromone from the myxobacterium Stigmatella aurantiaca that induces the formation of fruiting bodies, is described. Sharpless asymmetric epoxidation followed by tert-butyldimethylsilyl trifluoromethanesulfonate/Hünig’s base mediated intramolecular hydride ion transfer reactions were used to install the C-5 stereogenic center. Commercially available isovaleraldehyde is used as a starting material.
Key words
myxobacterium - fruiting body - Sharpless asymmetric epoxidation - hydride ion transfer - Wittig olefinationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589471.
- Supporting Information
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