93292-63-8Relevant articles and documents
Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)-Cytospolides D, e and Their Stereoisomers
Rej, Rohan Kalyan,Nanda, Samik
, p. 860 - 871 (2015/10/05)
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 accessed 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.
Addition of C-nucleophiles to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones: A new entry to thriomboxane analogues
Kirschning, Andreas,Harders, Jan
, p. 7867 - 7876 (2007/10/03)
Nucleophilic additions of silyl- and sulfur-stabilized carbanions 5a-e to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones 4a,b are described. Depending on the combination of substituents attached to the C1-anion, either 1,2- or 1,4-adducts are preferentially formed. Coupling of vinyl cuprate derived from 16 with enone 4a stereoselectively afforded pyranone 17 which is a potential precursor for thromboxane analogues.
TOTAL SYNTHESIS OF LIPOXINS A4 AND B4 FROM D-ISOASCORBIC ACID
Gravier-Pelletier, C.,Dumas, J.,Merrer, Y. Le,Depezay, J. C.
, p. 1165 - 1168 (2007/10/02)
A total convergent synthesis of lipoxins A4 and B4 has been carried out via four optically pure α-hydroxy and α,β-dihydroxyaldehydes, obtained from D-isoascorbic acid as a single starting material.Connection by a six carbons unit uses Wittig-type reaction
