Journal of the American Chemical Society, Vol.117, No.2, 634-644, 1995
Total Synthesis of Taxol .2. Construction of A-Ring and C-Ring Intermediates and Initial Attempts to Construct the ABC Ring-System
A method for the formation of Taxol’s ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol’s A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol’s B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.
Keywords:DESS-MARTIN PERIODINANE;LOW-VALENT TITANIUM;COUPLING REACTIONS;PYRIDINIUM CHLOROCHROMATE;SECONDARY ALCOHOLS;OXIDATION;KETONES;ACID;PROTECTION;PALLADIUM