A Stereocontrolled Total Synthesis of Lipoxin B4 and its Biological Activity as a Pro-Resolving Lipid Mediator of Neuroinflammation.

ABSTRACT: Two stereocontrolled, efficient, and modular syntheses of eicosanoid lipoxin B4 (LXB₄ ) are reported. One features a stereoselective reduction followed by an asymmetric epoxidation sequence to set the vicinal diol stereocentres. The dienyne was installed via a one-pot Wittig olefination and base-mediated epoxide ring opening cascade. The other approach installed the diol through an asymmetric dihydroxylation reaction followed by a Horner-Wadsworth-Emmons olefination to afford the common dienyne intermediate. Finally, a Sonogashira coupling and an alkyne hydrosilylation/proto-desilylation protocol furnished LXB₄ in 25 % overall yield in just 10 steps. For the first time, LXB₄ has been fully characterized spectroscopically with its structure confirmed as prev

SUBMITTER: Frank Lee C 

PROVIDER: S-EPMC9891714 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature