128142-68-7Relevant academic research and scientific papers
Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers
Rej, Rohan Kalyan,Nanda, Samik
, p. 860 - 871 (2014/03/21)
Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was ac- cessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.
CHIRAL α-HYDROXY- AND α,β-DIHYDROXY-ALDEHYDES FROM D-ISOASCORBIC AND L-ASCORBIC ACIDS. USEFUL PRECURSORS FOR THE SYNTHESIS OF FATTY ACID METABOLITES.
Merrer, Y. Le,Gravier-Pelletier, C.,Dumas, J.,Depezay, J. C.
, p. 1002 - 1006 (2007/10/02)
The four possible stereoisomers of α,β-dihydroxyaldehydes, useful building blocks for the synthesis of fatty acids metabolites, are synthesized via epoxy-tetrols derived from D-isoascorbic and L-ascorbic acids.The general method we develop allows the synthesis of chiral α-hydroxyaldehydes as well.
