CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES
CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES
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DOI：
10.1002/hlca.19790620629
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发表时间：
1979-01-01
影响因子：
1.8
通讯作者：
VASELLA, A
中科院分区：
文献类型：
--
作者：
BERNET, B;VASELLA, A
Carbocyclic Compounds from Monosaccharides. 1. Transformations in the Glucose SeriesA method for the preparation of pentasubstituted cyclopentanes from monosaccharides is presented, involving two crucial steps, viz. the reductive fragmentation of 5‐bromo‐5‐deoxyglucosides (such as10, 17and23, seeScheme 3) with Zn or butyl lithium yielding 5,6‐dideoxy‐hex‐5‐enoses (such as11and24, seeSchemes 3and4), and the subsequent cyclization of these hexenoses withN‐methyl‐ orN‐(alkoxyalkyl)hydroxylamines (viathe corresponding nitrones) to form cyclopentano‐isoxazolidines (seeScheme 2). Thus, the glucosides17and23were converted diastereoselectively and in good yields into the cyclopentano‐isoxazolidines27and45(Schemes 5and7), which were characterized by their transformation into various derivatives.27and45were correlated through the common derivative62. The configuration of the cyclization products were established by pyrolysis of theN‐oxide65to the enol ether67(Scheme 10).
