[structure] The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta-lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.
[reaction: see text] 6-Acetamido-5-amino- and -5-guanidino-3, 4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 and 9) have been synthesized starting from natural siastatin B, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors
The Journal of antibiotics, 49(1), 61-64 (1996-01-01)
Inhibitory activities of A-72363 A-1, A-2 and C, the diastereomers of a neuraminidase inhibitor siastatin B, against various glycosidases were tested in comparison to siastatin B. Despite these compounds differing only in their configuration, each compound showed strikingly different specificities
The Journal of antibiotics, 45(6), 963-970 (1992-06-01)
Siastatin B analogues, optically active 2-(trifluoroacetamide)- 3,4,5-trihydroxypiperidines having nitromethyl, aminomethyl and carboxyl branched groups at C-5, and (+)-(2R,3R,4R,5R)-5-(aminomethyl)-3,4,5-trihydroxy-2- (hydroxyacetamido)piperidine have been obtained total synthetically from D-ribono-1,4-lactone. Some analogues have inhibitory activity against some glycosidases, and (+)-(2R,3R,4R,5R)-2-(trifluoroacetamido)-3,4,5-trihydroxypiperi dine-5-carboxylic acid showed a
The Journal of antibiotics, 46(12), 1883-1889 (1993-12-01)
Two epimers of siastatin B, 3-episiastatin B (3) and 3,4-diepisiastatin B (4), were obtained by the chemical modification of siastatin B. Compound 3 showed marked inhibitory activity against influenza virus neuraminidases and significant inhibition of influenza virus infection in vitro.
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