Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst.
Genki KawauchiShigenobu UmemiyaTohru TaniguchiKenji MondeYujiro HayashiPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
An enantioselective total synthesis of latanoprost was achieved. Its chiral cyclopentane core structure was constructed through an organocatalyst-mediated [3+2]-cycloaddition reaction, and chirality in the ω-side chain was generated by prolinate-anion-mediated α-aminoxylation of an aldehyde. Highly diastereoselective domino acetalization and an oxy-Michael reaction were key steps for the generation of C9 chirality.