(E)-Bis-1,2-(tributylstannyl)ethylene as a staple in a synthetic approach to taxol

✍ Scribed by Francette Delaloge; Joëlle Prunet; Ange Pancrazi; Jean-Yves Lallemand

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 287 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02306-4

✦ Synopsis

An approach of taxol synthesis based on the use of (E)-bis-l,2-(tributylstannyl)ethylene 6 as a readily available two-carbon 1,2-1ink between A and C-ring is described, The conjugate addition of a mixed higher-order stannylvinyl cyanocuprate derived from 6 on chkal cyclobexenone $ is completely stereoselective. A model study on 3-methylcyclohex-2-enone showed that the afforded stannylvinyl cyclohexenone 12 c,~ be engaged without further transformation in a Stifle cross-coupling reaction with the vinyl Iriflate 4 corresponding to the A-ring of taxol to give seco-taxane 14.