Total syntheses of N-trifluoroacetyl-L-daunosamine, N-trifluoroacetyl-L-acosamine, N-benzoyl-D-acosamine, and N-benzoyl-D-ristosamine from an achiral precursor, methyl sorbate

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作者：
Ono, M
Saotome, C
Akita, H
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来源：
HETEROCYCLES | 1997年 / 45卷 / 07期
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy) -(2E)-hexenoate (12) followed by lactonization under acidic condition proceeds formally to the total syntheses of L-daunasamine (1) and L-acosamine (2). On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate (4) and the subsequent intramolecular nucleophilic attack by ester carbonyl group against epoxy ring of the substrates leads to the formal total syntheses of D-acosamine (2) and D-ristosamine (3).
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页码：1257 / 1261
页数：5
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