Synthetic study of microtubule-stabilizing agents

以苹果酸二甲酯为原料，通过化学和立体选择性催化的C-H插入反应和空间位阻的酮的Baeyer-Villiger反应作为关键步骤，合成了(2S)-2-tert-butyldimethylsilyloxy-3-[(2S，3S，4S，5R)-4-tert-butyldimethyl-silyloxy-3，-5-二甲基-6-氧代四氢吡喃-2-丙醛。劳利马利特的正式合成包括氧叶立德形成-[3，3]-Sigmatrotic重排反应和SN型环化反应。

Formal syntheses of microtubule-stabilizing agents, discodermolide and laulimalide were achieved.Synthesis of discodermolide was started from dimethyl (R)-malate by using chemo-and stereoselective dirhodium catalyzed C-H insertion reaction and novel acceleration technique of Baeyer-Villiger reaction of sterically hindered ketones as key steps to give (2S)-2-tert-butyldimethylsilyloxy-3-[(2S,3S,4S,5R)-4-tert-butyldimethyl-silyloxy-3, 5-dimethyl-6-oxotrahydropyran-2-yl]propanal, Smiths intermediate of their total synthesis of discodermolide. Formal synthesis of laulimalide was included oxonium ylide formation-[3,3]-sigmatropic rearrangement reaction and SN type cyclization as key steps.