Enantioselective total synthesis of cis-(+)- and trans-(+)-disparlure

• Published in: Tetrahedron letters Vol. 58; no. 34; pp. 3344 - 3346
• Main Authors: Garg, Yuvraj, Kumar Tiwari, Anand, Kumar Pandey, Satyendra
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.08.2017; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Disparlure; MacMillan’s self aldol reaction; Mitsunobu esterification; Physical Sciences; Science & Technology; Sex-attractant pheromone; Wittig olefination; MacMillan’s self aldol reaction; Sex-attractant pheromone; Disparlure; Wittig olefination; Mitsunobu esterification; RESOLUTION; ENANTIODIVERGENT SYNTHESIS; (+)-DISPARLURE; PHEROMONE ENANTIOMERS; IDENTIFICATION; GYPSY-MOTH; MacMillan's self aldol reaction; (-)-DISPARLURE; SEX ATTRACTANT
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.07.024

[Display omitted] •cis-(+)-Disparlure, a female gypsy moths sex pheromone.•A concise and efficient asymmetric general approach for disparlure.•Organocatalytic MacMillan’s self aldol reaction and Wittig olefination key steps.•Regioselective ring opening of an epoxide and Mitsunobu esterification reactions. An expedient enantioselective synthetic approach for the gypsy moth sex-attractant pheromone cis-(+)-1 and trans-(+)-disparlure 2 is described employing the optimized combination of organocatalytic MacMillan’s self aldol reaction, Wittig olefination, regioselective ring opening of an epoxide and Mitsunobu esterification reactions as key steps.