84184-35-0Relevant academic research and scientific papers
STEREOCONTROL BY INTRODUCTION OF A SULFUR FUNCTIONAL GROUP IN THE ASYMMETRIC REDUCTION OF β-KETOESTERS WITH BAKER'S YEAST: PREPARATION OF OPTICALLY PURE 3S-HYDROXYDITHIOESTERS AS A NEW CHIRAL SYNTHON OF NATURAL PRODUCT SYNTHESIS
Itoh, Toshiyuki,Yonekawa, Yoshihiro,Sato, Toshio,Fujisawa, Tamotsu
, p. 5405 - 5408 (1986)
Asymmetric reduction of β-ketothioester derivatives with baker's yeast produced the corresponding optically pure 3S-hydroxythioesters, which are useful chiral building blocks in organic synthesis.The utility of the present method was demonstrated in the stereoselective synthesis of sex attractant of pine saw-fly, (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate from the 3S-hydroxy esters.
Stereospecific Synthesis of (2R,5R)-Hept-6-yne-2,5-diamine: A Potent and Selective Enzyme-activated Irreversible Inhibitor of Ornithine Decarboxylase (ODC)
Casara, Patrick,Danzin, Charles,Metcalf, Brian,Jung, Michel
, p. 2201 - 2208 (2007/10/02)
Hept-6-yne-2,5-diamine (2) and 2-methylhept-6-yne-2,5-diamine (3), while structurally related to the potent ornithine decarboxylase (ODC) inhibitor hex-5-yne-1,4-diamine (1), are stable to in vivo oxidation by monoamine oxidase (MAO).Although the methyl substitution is at a carbon relatively remote from the site of metabolic attack by ornithine decarboxylase (ODC), it has a critical influence on the potencies of these compounds as inhibitors of the enzyme.Of the four stereoisomers, (2R,5R)-(2) is the most active.Unambiguous syntheses of each isomer of (2) from the dianion of 3-trimethylsilyl-N-butoxycarbonylprop-2-ynylamine (5) are presented.
