129083-14-3Relevant articles and documents
First total synthesis of the anti-inflammatory lipid mediator Resolvin D6
Rodriguez, Ana R.,Spur, Bernd W.
, p. 86 - 89 (2012)
The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.
Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates
Rodriguez, Ana R.,Spur, Bernd W.
, p. 5811 - 5815 (2015/09/29)
The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs2CO3 promoted coupling provided the skipped diyne intermediate. Wittig reactions and epoxide opening with glutathione, l-cysteinylglycine, and l-cysteine methyl ester hydrochloride, respectively, were the key steps in the synthesis.
Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development
Yadav,Somaiah,Ravindar,Chandraiah
, p. 2848 - 2850 (2008/09/20)
An efficient stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development, is described. Highlights of the strategy include the utilization of Sharpless asymmetric epoxidation, Yamaguchi lactonization and an olefin cross-metathesis as the key steps.
An Improved Asymmetric Epoxidation of Allyl Alcohols using Titanium-pillared Montmorillonite as a Heterogeneous Catalyst
Choudary, B. M.,Valli, V. L. K.,Prasad, A. Durga
, p. 1186 - 1187 (2007/10/02)
A simple and convenient procedure for the catalytic asymmetric epoxidation of primary allyl alcohols with high enantiomeric purities and good yields using a heterogeneous titanium-pillared montmorillonite catalyst is demonstrated.
