ChemInform Abstract: Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)‐Taxusin and (‐)‐Taxol

Abstract

To construct taxane ABC tricarbocycles, a useful methodology including an aldol-like eight-membered B ring cyclization between dienol silyl ethers and acetals was explored. By applying this methodology, the enantioselective total syntheses of (+)-taxusin and (-) -taxol have been achieved, starting from the substrate containing a chiral center at each C1 site, based on AC to ABC strategies. Syntheses of several artificial taxoids are also described. 4Enantioselective Total Synthesis of (-)-Taxol 4.1 Synthetic Plan 4.2 Enantioselective Synthesis of the A-ring fragment 4.3 From A to AC and to ABC Tricarbocycles 4.4 Introduction of the C19 Methyl Group 4.5 Functional Group Manipulation for Total Synthesis of (-)-Taxol 5 Synthesis of Taxane Analogs 6 Conclusion