合成路线1

The Wittig condensation of methyl 7-(5alpha-acetoxy-2beta-formyl-3alpha-hydroxycyclopent-1-yl)heptanoate (I) with dimethyl 3-mothoxy-3-methyl-2-oxoheptyl phosphonate (II) by means of NaH in dimethoxy ethane gives methyl 9alpha-acetoxy-11alpha-hydroxy-16-methoxy-16-methyl-15-oxoprosta-13-en-1-oate (III), which is treated with dihydropyran and p-toluenesulfonic acid to yield the 11alpha-tetrahydropyranyloxy derivative (IV). The reduction of (IV) with NaBH4 in methanol affords methyl 9alpha-acetoxy-15-hydroxy-16-methoxy-16-methyl-11alpha-(tetrahydropyranyloxy)prosta-13-en-1-oate (IV), which is protected again with dihydropyran as before to give the 11,15-bis(tetrahydropyranyloxy) derivative (VI). The hydrolysis of the acetoxy group of (VI) with K2CO3 in methanol affords methyl 9alpha-hydroxy-16-methoxy-16-methyl-11alpha,15-bis(tetrahydropyranyloxy)prosta-13-en-1-oate (VII), which is oxidized with Collins' reagent (CrO3-pyridine) in methylene chloride yielding methyl 16-methoxy-16-methyl-9-oxo-11alpha,15-bis(tetrahydropyranyloxy)prosta-13-en-1-oate (VIII). Finally, this compound is deprotected by a treatment with acetic acid in THF - water.