First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid

Synthesis of Enantiomerically Pure (8S,9S,10R,6Z)-Trihydroxyoctadec-6-enoic Acid

“…5b In 2011, Sharma and his co-workers reported the synthesis of (6S,9R,10S,7E)-6,9,10-trihydroxyoctadeca-7-enoic acid starting from protected glyceraldehyde as a chiral template, followed by two organometallic additions to aldehyde and alkene-cross metathesis. 6 In 2012, Narsaiah and his-workers reported the synthesis of (6R,9R,10R,7E)-6,9,10-trihydroxyoctadec-7-enoic acid starting from n-decanal using Sharpless asymmetric dihydroxylation and CBS reduction to build the chiral center. 7 Barua et al reported oxylipin-related compounds using Lascorbic acid and Jacobsen's hydrolytic kinetic resolution.…”

“…8 More recently, Yadav and his co-workers reported the related compounds starting from D-ribose as a chiral pool. 9 On the other hand, we reported the enantioselective allylic oxidation of 4,5-epoxycyclohex-1-ene (6) with tert-butyl perbenzoate, a catalytic amount of a chiral S-configured N,Nbidentate ligand, and a copper catalyst. This reaction afforded (3S,4S,5S)-3-benzoyl-4,5-epoxycyclohex-1-ene, with 84% ee.…”