Carbocyclische Verbindungen aus Monosacchariden. I. Umsetzungen in der glucosereihe

Helvetica Chimica Acta - Tập 62 Số 6 - Trang 1990-2016 - 1979
Bruno Bernet1,2, Andrea Vasella1,2
1Institut für Organische Chemie der Universität, Pérolles, CH-1705 Freiburg i. Ü.
2Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule Zürich, CH-8092 Zürich

Tóm tắt

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 as 10, 17 and 23, see Scheme 3) with Zn or butyl lithium yielding 5,6‐dideoxy‐hex‐5‐enoses (such as 11 and 24, see Schemes 3 and 4), and the subsequent cyclization of these hexenoses with N‐methyl‐ or N‐(alkoxyalkyl)hydroxylamines (via the corresponding nitrones) to form cyclopentano‐isoxazolidines (see Scheme 2). Thus, the glucosides 17 and 23 were converted diastereoselectively and in good yields into the cyclopentano‐isoxazolidines 27 and 45 (Schemes 5 and 7), which were characterized by their transformation into various derivatives. 27 and 45 were correlated through the common derivative 62. The configuration of the cyclization products were established by pyrolysis of the N‐oxide 65 to the enol ether 67 (Scheme 10).

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Helvetica Chimica Acta

Tập 62 Số 6

1990-2016

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