Unexpected rearrangement during biomimetic entry toward a taxane skeleton

✍ Scribed by Mugio Nishizawa; Hiroshi Imagawa; Ikumi Hyodo; Miho Takeji; Eiko Morikuni; Kohsuke Asoh; Hidetoshi Yamada

• Book ID: 104258502
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 255 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10556-1

✦ Synopsis

Bicyclo[9.3.1 ]

pentadecatriene derivative 4 which corresponds to a precursor of taxol in a biomimetic entry was constructed by means of TiC14-Zn promoted McMurry cyclization and Mitsunobu inversion. Treatment of 4 with mercuric triflate afforded an unexpected rearrangement-transannular cyclization product 5.