Synthesis with organoboranes. 21. Synthesis of α- and gd-bamascone

✍ Scribed by Marek Zaidlewicz

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 267 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85153-9

✦ Synopsis

Selective syntheses of at-and t-damascone, using allylic organoboranes a9 the key intermediates, are described.

Damascones and closely related dsmascenones are important carotgnoid aroma compounds. The isolation of p-dawasoenone from Bulgarian rose oil , stimulated a great interest in these compounds. Their occurrence and chemistry have been reviewedTs5 ac-Damascone /i/4-6 and b-damascone /~/4~5~7-13 have been prepared by various methods. Only recently, however, selective routes to 2 starting from readily available materials have been worked out?"13 In these preparations the exocyolic double bond formed via ylide8 and the side chain are introduced in separate Steps.