A facile synthesis of a Δ2-cedrene skeleton via tandem radical cyclization

✍ Scribed by Yao-Jung Chen; Wen-Yuan Lin

• Book ID: 104224791
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 141 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91723-4

✦ Synopsis

A facile synthesis of a A*-cedrene skeleton via tandem radical cyclization is described. The tricyclic sesquitetpene A2-cedrene la, an isomer of a-cedrene, has been found in vetiver oil by Kaiser et al in 1972.' previous strategies used for the construction of the tricyclo[5.3.1.0'S5]undecane skeleton have included sequential cyclizations through carbonium ion intermediates,* intramolecular Diels-Alder reaction3 an intramolecular 1,3-photocycloaddition reaction4 sequential inter-and intra-molecular Michael reactions,5 and Claisen cyclization6

We now outline a new and facile synthesis of (+)-A*-8-epicedrene lb via tandem radical cyclization?

Our retro-synthetic analysis involving a single step tandem radical cyclization strategy is outlined below.