Abstract
An approach of taxol synthesis based on the use of ( E)-bis-1,2-(tributylstannyl)ethylene 6 as a readily available two-carbon 1,2-link between A and C-ring is described. The conjugate addition of a mixed higher-order stannylvinyl cyanocuprate derived from 6 on chiral cyclohexenone 5 is completely stereoselective. A model study on 3-methylcyclohex-2-enone showed that the afforded stannylvinyl cyclohexenone 12 can be engaged without further transformation in a Stille cross-coupling reaction with the vinyl triflate 4 corresponding to the A-ring of taxol to give seco-taxane 14.
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