Total synthesis of the hypocholesterolemic agent compactin

Article abstract of DOI:10.1021/ja00341a046

A total synthesis of ( plus )-compactin (ML-236B), a potent inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase, is presented. The key chiral hexahydronaphthalene intermediate was efficiently synthesized in 70% overall yield from the optically active diol. In turn, the diol was obtained via microbiological reduction of the racemic dione. ( plus )-Compactin was prepared in 14 steps from the chiral hexahydronaphthalene intermediate in 0. 8% yield. Refs.