Organocatalyst-mediated, pot-economical total synthesis of latanoprost.

ABSTRACT: The enantioselective total synthesis of latanoprost, an antiglaucoma agent, has been accomplished with excellent diastereo- and enantioselectivities in a pot-economical manner using six reaction vessels. An enantioselective Krische allylation was conducted in the first pot. In the second pot, olefin metathesis, silyl protection, and hydrogenolysis proceeded efficiently. In the third pot, an organocatalyst-mediated Michael reaction proceeded with excellent diastereoselectivity. The fourth pot involved a substrate-controlled Mukaiyama intramolecular aldol reaction and elimination of HNO₂ to afford a methylenecyclopentanone, also with excellent diastereoselectivity. The fifth pot involved a Michael reaction of vinyl cuprate. In the sixth pot, three reactions, a cis-selective

SUBMITTER: Kawauchi G 

PROVIDER: S-EPMC10530343 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature