283151-73-5Relevant academic research and scientific papers
Baker's yeast reduction of β-hydroxy ketones
Acetti, Daniela,Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Serra, Stefano
experimental part, p. 142 - 151 (2010/03/24)
Reduction of β-hydroxy ketones to the corresponding 1,3-diols by baker's yeast was investigated, in order to develop methods for simultaneous control over the configurations of multiple stereogenic centres. The reactions were found to be enantiospecific a
A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms
Ahmad,Taneja,Singh,Anand,Qurishi,Koul,Qazi
, p. 445 - 450 (2007/10/03)
Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (1R,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1,3-but
Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols
Vicario, Jose L.,Badia, Dolores,Dominguez, Esther,Rodriguez, Monica,Carrillo, Luisa
, p. 3754 - 3759 (2007/10/03)
A very efficient method for performing stereoselective aldol reactions is reported. The reaction of (S,S)-(+)-pseudoephedrine-derived propionamide enolates with several aldehydes yielded exclusively one of the four possible diastereomers in good yields, although transmetalation of the firstly generated lithium enolate with a zirconium(II) salt, prior to the addition of the aldehyde, is necessary in order to achieve high syn selectivity. The so-formed syn-α-methyl-β-hydroxy amides were transformed into other valuable chiral nonracemic synthons such as α-methyl-β-hydroxyacids, esters, and ketones. Finally, a stereocontrolled reduction procedure starting from the so-obtained α-methyl-β-hydroxy ketones has been developed allowing the synthesis of either 1,3-syn- or 1,3-anti-α-methyl-1,3-diols in almost enantiopure form by choosing the appropriate reaction conditions.
Total synthesis of (+)-conagenin
Hatakeyama, Susumi,Fukuyama, Hiroko,Mukugi, Yasuko,Irie, Hiroshi
, p. 4047 - 4050 (2007/10/03)
The first total synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved in highly stereo- and enantioselective manner. The carboxylic acid moiety was synthesized starting with asymmetric aldor reaction of propiophenone with acetaldehyde followed by in situ syn-selective NaBH4 reduction. The amin acid moiety was synthesized based upon Et2AlCl catalyzed cyclization of the epoxy trichloroacetimidate prepared from (S)-methylglycidol. Condensation of both moieties and alkaline hydrolysis led to (+)-conagenin.
