93292-63-8Relevant 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 (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.
A chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids
Sharma, Anubha,Mahato, Seema,Chattopadhyay, Subrata
scheme or table, p. 4986 - 4988 (2009/12/03)
A brief and facile synthesis of the title compounds has been developed by using an efficient lipase-catalyzed acylation and a chiral template-directed diastereoselective alkylation for incorporating the stereogenic centres. A cross-metathesis was employed to get the required E-olefin geometry.
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.
A versatile route to conjugated hydroxy (E,Z,E,E)-tetraenoic acids: Highly chemo- and stereoselective synthesis of lipoxin B4
Alami, Mouad,Crousse, Benoit,Linstrumelle, Gerard,Mambu, Lengo,Larcheveque, Marc
, p. 2949 - 2958 (2007/10/03)
A highly convergent total stereocontrolled synthesis of lipoxin B4 is described by an efficient Pd-catalyzed coupling reaction of two easily accessible chiral synthons 2 and 3 without any protection-deprotection sequence of the alcohol function
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
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.
Transformations of Tartaric Acid. Complementary Methods for the Synthesis of Optically Active α-Hydroxyaldehyde Derivatives
Achmatowicz, Barbara,Wicha, Jerzy
, p. 267 - 276 (2007/10/02)
Methods for the synthesis of (R)- and (S)-2-benzyloxy and 2-(t-butyldiphenylsilyloxy)-aldehydes from optically active tartaric acids are described.
TRANSFORMATION OF TARTARIC ACID: A FACILE SYNTHESIS OF DERIVATIVES OF OPTICALLY ACTIVE α-HYDRXYOALDEHYDES
Achmatowicz, Barbara,Wicha, Jerzy
, p. 2999 - 3002 (2007/10/02)
Methods for synthesis of (R)- and (S)-2-benzyloxy- and 2-(t-butyldiphenylsilyloxy)-aldehydes from optically active tartaric acids are described.
