The first total synthesis of sporiolide A.
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.
Du
Yuguo
Y
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. duyuguo@rcees.ac.cn
Chen
Qi
Q
Linhardt
Robert J
RJ
D002125:Calcium Gluconate / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis / Q000737:chemistry; D014994:Xylose / Q000737:chemistry
D007783:Lactones; D004364:Pharmaceutical Preparations; C521690:sporiolide A; D014994:Xylose; D002125:Calcium Gluconate