The total synthesis of (-)-Tax01 has been achieved. Functional group manipulation of diol 2 provided the ABC ring system with the correct C9-keto, C10-acetyloxy functionality. Careful optimization allowed the oxidation of the C5-C6 alkene in 4 at C5 via a hydroboration reaction. Functional group manipulation of this product, 29, provided, through two routes, the oxetane D ring as 36. Following the method developed by degradative studies provided the natural enantiomer of Taxol (1).

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 McMuny ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMuny reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,ClO-diol (f)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.