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High pressure approach to the total synthesis of 6-EPI-d-purpurosamine b

✍ Scribed by Adam Gołȩbiowski; Janusz Jurczak; Ulla Jacobsson

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
310 KB
Volume
43
Category
Article
ISSN
0040-4020

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✦ Synopsis

Methyl 2,6-di-I-acetyl-6-epia-&-purpurosaminide B (11) was synthesized from L-alanine by an eleven-step reaction sequence. Eu(fod)a-mediated high-pressure (4t2)cycloaddition of 1-methoxybuta-1,3-diene (2) to a-amino aldehyde 3, easily available from Galanine (A), is the key step in the synthetic sequence. 2,6-Diamino-2,3,4,6,7-pentadeoxy-L-lyxo-heptopyranose, commonly named 6-epi-g-purpurosamine B (l), is apart from aminocyclitol fortamine. a component of an aminoglycosidic antibiotic fortimicin. 1.2 The &protected derivatives of 1 have recently been synthesized by two Japanese groups: Suami et al. 3 and Yasuda et al. 4 In both methods, 2-amino-2-deoxy-Q-glucose served as starting material,

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