Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent
Enantioselective synthesis of the hexahydroazepine core of (?)-balanol and formal synthesis of cis-3-hydroxypipecolic acid from a common intermediate have been accomplished by a divergent path. The common intermediate was accessed from a favorably protected enantiomerically pure 2-amino-1,3,4-butanetriol (ABT) equivalent via oxidation and Wittig olefination. The synthesis of (?)-balanol heterocycle featured tandem reduction/acetal-deprotection/γ-lactonization reaction and a one-pot azide reduction followed by seven membered aza-heterocycle formation while the route to cis-3-hydroxypipecolic acid highlighted the base induced piperidine ring formation and regioselective benzylidine-acetal cleavage.
Chavan, Subhash P.,Kalbhor, Dinesh B.,Gonnade, Rajesh G.
(2021/01/14)
ACYCLIC AMINE INHIBITORS OF NUCLEOSIDE PHOSPHORYLASES AND HYDROLASES
The invention relates to compounds of the general formula (I) which are inhibitors of purine nucleoside phosphorylases (PNPs) and/or nucleoside hydrolases (NHs). The invention also relates to the use of these compounds in the treatment of diseases and infections including cancer, bacterial infections, protozoal infections, and T-cell mediated disease and to pharmaceutical compositions containing the compounds.
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Page/Page column 49
(2008/06/13)
Intermediates and synthesis of 2-amino-2-deoxytetritols
Novel methods are provided for synthesizing 2-amino-2-tetritol, by positive halogen addition to protected 1,4-dioxybutene-2 in the presence of a nitrile, resulting in addition of a halo functionality and the nitrile functionality across the double bond. Upon hydrolysis, the desired erythro-product can be obtained in stereochemically good yield.
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(2008/06/13)
Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media
Novel intermediates for non-ionic polyiodo amino-substituted benzenepolyamides having polyol substituents on the amide nitrogens are provided which are 5-amino-6-hydroxy-1,3-dioxepanes. The compounds provide an economic and efficient route to novel contrast media having excellent chemical and physiological properties. Also provided are methods for preparing the subject compounds.
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(2008/06/13)
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