Patent ID: 8476471

Claim:
A method of preparing a prostaglandin or prostaglandin analog, the method comprising: providing a compound of Formula (I): wherein: n and m are integers between 0 and 4, wherein n+m is 3 or 4; R 1 is H or a hydroxyl protecting group; R 2 is H, alkyl or aralkyl, optionally wherein the alkyl or aralkyl group further comprises one or more alkyl or aryl group substituents; R 3 and R 4 are independently H or alkyl; and the substituents at carbons 1 and 2 of the cyclopentane ring are oriented cis to one another and trans to the substituent at carbon 3; reacting the compound of Formula (I) with a transition metal carbene complex catalyst to perform a ring closing metathesis reaction, thereby forming a lactone; and reacting the lactone with a nucleophile to form a ring-opened product, wherein said ring-opened product is a prostaglandin, prostaglandin analog or synthetic intermediate thereof, wherein said prostaglandin or prostaglandin analog has the formula: wherein m, n, R 1 , R 2 , R 3 , and R 4 are as defined above; X′ is selected from the group consisting of —OH, —SH, —NH 2 , —O-alkyl, —O-aryl, —S-alkyl, —S-aryl, —NH-alkyl, —NH-aryl, —NH-aralkyl, —NH-sulfonyl-alkyl, —NH-sulfonyl-aryl, —N(alkyl) 2 , —N(aryl) 2 , and —N(alkyl)(aryl); and the substituents at carbons 1 and 2 of the cyclopentane ring are oriented cis to one another and trans to the substituent at carbon 3.