Synthesis of 3-Oxa-guaianolides from Santonin

✍ Scribed by Gonzalo Blay; Luz Cardona; Begoña Garcı́a; Luisa Lahoz; Belén Monje; José R Pedro

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 148 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00571-8

✦ Synopsis

AbstractÐThis article reports on the transformation of santonin into two C 10 -epimeric 3-oxa-guaianolides which are 8-deoxyderivatives of several natural 3-oxaguaianolides isolated from Achillea species. The synthesis involved the photochemical rearrangement of the eudesmane skeleton into a guaiane skeleton and the transformation of the cyclopentane ring into a furan moiety with the concomitant loss of C 3 . Comparison of the NMR data of the synthetic products with those of the natural products con®rms the b orientation of the hydroxyl group at C 10 in the products isolated from Achillea.