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Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction
Hiroaki Matoba1, Takahiro Watanabe1, Masanori Nagatomo1
1Graduate School of Pharmaceutical Science , The University of Tokyo , Hongo, Bunkyo-ku, Tokyo 113-0033 , Japan.
Abstract:
The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.
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