Stereoselective Total Synthesis of (S)-Stigmolone: A Fruiting-Body-Inducing Pheromone

Yadav, Jhillu ; Srihari, Pabbaraja ; Kumar, A. ; Alghamdi, Ahmad (2016) Stereoselective Total Synthesis of (S)-Stigmolone: A Fruiting-Body-Inducing Pheromone Synthesis, 49 (07). pp. 1702-1706. ISSN 0039-7881

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Official URL: http://doi.org/10.1055/S-0036-1589471

Related URL: http://dx.doi.org/10.1055/S-0036-1589471

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.

Item Type:Article
Source:Copyright of this article belongs to Georg Thieme Verlag KG.
ID Code:135699
Deposited On:10 Aug 2023 10:03
Last Modified:10 Aug 2023 10:03

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