Synthesis of 1,4-Diaminocyclitols From l-Serine Methyl Ester

l-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)6]2[Zn2Cl6] (1) gave C 2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-08, Vol.61 (16), p.5528-5531
Main Authors: Kang, Min, Park, Jeonghan, Konradi, Andrei W, Pedersen, Steven F
Format: Article
Language:English
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Summary:l-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)6]2[Zn2Cl6] (1) gave C 2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo960691a