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Synthesis of the Oviposition-Deterring Pheromone (ODP) in Rhagoletis cerasi L. Preliminary communication (1989)

Ernst, Beat ; Wagner, Beatrice

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 72 (1989), S. 165-171

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: For the assignment of the configuration at C(8) and C(15) of the natural oviposition-deterring pheromone 1 in Rhagoletis cerasi L., the four possible stereoisomers of 1 are synthesized. By condensing the C6 building blocks (5R)-4 and (5S)-4 with the boron enolates of the C10 building blocks (4S)-13 and (4R)-13, followed by decarboxylative dehydration, all stereoisomers of 16 are available (Scheme 5). Glucosylation of 16 followed by formation of the taurin amide gives, after deprotection, the four stereoisomers (8R,15S)-1, (8R,15R)-1, (8R,15S)-1, and (8S,15S)-1 (Scheme 6).

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19890720122

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