화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.117, No.2, 645-652, 1995
Total Synthesis of Taxol .3. Formation of Taxols ABC Ring Skeleton
The synthesis of Taxol’s ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the CB,C10-diol (+/-)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.