An efficient synthesis of (-)-posticlure: The sex pheromone of Orgyia postica

European Journal of Organic Chemistry

Volumn , Issue 30, 2007, Pages 5064-5070

  Fernandes, Rodney A ^a  

^a Instituto de Quimica de la UNAM   (Mexico)

Author keywords

Asymmetric synthesis; Diethyl L tartrate; Epoxides; Orgyia postica; Pheromones

Indexed keywords

EID: 35548984925     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700449     Document Type: Article

References (20)

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4. b) In February 2004 a new pherolist was created by Peter Witzgall, Tobias Lindblom, Marie Bengtsson and Miklós Tóth: http://www-pherolist. slu.se/pherolist.php.
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12. 3).
13. 3) in b) E. Hungerbuhler, D. Seebach, Helv. Chim. Acta 1981, 64, 687-702.
14. 3, filtration, concentration and column chromatography, afforded the mixture in the same ratio. For a similar conversion of vicinal diols to monoacetoxy products using trimethyl orthoacetate, see: M. Ikejiri, K. Miyashita, T. Tsunemi, T. Imanishi, Tetrahedron Lett. 2004, 45, 1243-1246.
15. If the cyclic orthoacetate was stable to multistep reactions we could save one step in the synthetic strategy, that is, route A vs. route B (see Scheme 1).
16. The intermediates are shown below. The cyclic orthoacetate is formed as exemplified by this conversion, though probably it is not stable to isolation. (Chemical Equation Presented)
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