C-nucleosides. Part 2. Preparation of 2-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]thiazole-4-carboxamide (‘carbocyclic’ tiazofurin) and its antipode

Autor:	David C. Humber, Richard J. Stoodley, Allan P. Dishington
Rok vydání:	1993
Předmět:	medicine.drug_class Stereochemistry Diastereomer Carboxamide chemistry.chemical_compound chemistry medicine Lactam Hydroxymethyl Triol Enantiomer Thiazole Tiazofurin medicine.drug
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :57-65
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19930000057
Popis:	Benzyl β-aminopenicillanate 1β-oxide 9c underwent N-acylation with (1R*,2S*,3R′,4R*)-2,3-dibenzoyloxy-4-(benzoyloxymethyl)cyclopentanecarbonyl chloride 11b—assembled in nine steps from trinorbornadiene—to give a mixture of the penicillins 10d and 13c, which were readily separated by chromatography. The less polar material, identified as the diastereoisomer 10d by its conversion into (1R,5R,6R,7S)-6,7-isopropylidenedioxy-3-oxabicyclo[3.2.1]octan-2-one 24, was transformed into the title compound 1b by a four-step sequence. In a similar manner, the penicillin 13c was converted into carbatiazofurin enantiomer ent-1b. Both carbatiazofurin 1b and its enantiomer displayed cytotoxicity against a breast carcinoma cell line.
Databáze:	OpenAIRE
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