Fragmentations of 13-oxo-taxyunnansin A and their application to preparation of abeo-paclitaxel and abeo-docetaxel analogues

Two interesting unprecedented fragmentations of 13-oxo-taxyunnansin A (3), initiated by treatment with tBuOK and Red-Al, respectively, have been discovered, optimized and successfully applied to the synthesis of novel abeo-paclitaxel and abeo-docetaxel derivatives. Eight new derivatives of abeo-paclitaxel and abeo-docetaxel possessing the structurally simplified 11 (15→1)-abeo-taxane skeleton with an oxetane ring and π bond conjugate system were accordingly prepared for the further evaluation of anticancer activities.