Du Yuguo, Chen Qi, Linhardt Robert J
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
J Org Chem. 2006 Oct 27;71(22):8446-51. doi: 10.1021/jo0615504.
The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.
天然细胞毒性剂sporide A的首次全合成已从D-葡萄糖烯出发，经16步反应完成，总产率为6.1%。在合成过程中，碳水化合物被用作手性模板来控制绝对构型。吡啶氯铬酸盐（PCC）促进的环状烯醇醚向内酯的转化，随后进行山口酯化和分子内环化复分解反应，极大地促进了目标化合物的合成。
