ChemInform Abstract: Synthesis of Carbasugars from Aldonolactones. Part 2. Preparation of Polyhydroxy/aminocyclopentanes Functionalized at All Five Ring Carbons.
Abstract
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ChemInform Abstract
Four sugar mimics (VIII), (IX), (XII), and (XV) are prepared from the easily available bromo acetate (I). It is found that the stereoselectivity of the OsO4-catalyzed dihydroxylation step of allylic derivatives (II) depends on the size of the substituent at the hydroxy group and gives either predominantly or exclusively exo or endo products (IV), (V), or (XVI). Regioselective ring opening of lactones derived from (IV) or (V) is achieved either with in situ generated Ca(BH4)2 to give, after deprotection, the target compounds (VIII), (IX), and (XII) or with Ca(BH4)2×2THF complex to afford finally mimic (XV).
