Preparation of optically active derivatives of (1,4/2,3,5)- and (1,2,3,4,5/0)-5-aminocyclopentane-1,2,3,4-tetraols: synthesis of mannostatin A and its enantiomer
Seiichiro Ogawa, Hiroshi Kimura, Chikara Uchida, Takashi Ohashi
Abstract
Seiichiro Ogawa, Hiroshi Kimura, Chikara Uchida, Takashi Ohashi
Abstract
Diastereoselective acylation of the 2,3-O-cyclohexanediyl derivatives of (1,4/2,3,5)- and (1,2,3,4,5/0)-5-acetamidocyclopentane-1,2,3,4-tetraols with some optically active chiral acids afforded, with moderate diastereoselectivity, the chiral monoesters useful as synthetic intermediates, from which mannostatin A and its enantiomer were synthesized.
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Diastereoselective acylation of the 2,3-O-cyclohexanediyl derivatives of (1,4/2,3,5)- and (1,2,3,4,5/0)-5-acetamidocyclopentane-1,2,3,4-tetraols with some optically active chiral acids afforded, with moderate diastereoselectivity, the chiral monoesters useful as synthetic intermediates, from which mannostatin A and its enantiomer were synthesized.
Key concepts: Enantiomer, Optically active, Acylation, Chemistry, Combinatorial chemistry, Stereochemistry, Organic chemistry, Catalysis