Tetrahedron

An enantioselective synthesis of (+)-bostrycin leading to a revision of the absolute configuration of its natural antipode

DS Larsen, RJ Stoodley

文献索引：Larsen, David S.; Stoodley, Richard J. Tetrahedron, 1990 , vol. 46, # 13-14 p. 4711 - 4732

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被引用次数: 21

摘要

An asymmetric Diels-Alder reaction, involving the protected naphthopurpurin (4) and the D- glucose-derived diene (9a), is used to assemble compound (22), which is transformed by way of compounds (26),(27) and (28) into (+)-bostrycin (3). An X-ray analysis of compound (28) confirms that (+)-bostrycin possesses the stereostructure (3) and, therefore, that (-)- bostrycin is its antipode, ie (2). The use of naphthazarin (14a) and juglone (14c) as ...