ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of 3-O-carbamoyl-noviose, the carbohydrate of the antibiotic novobiocin, is described. Starting with D-glucose the synthesis comprises a number of steps (1-5) up to the important intermediate 3,5,6-tri-O-benzyl-2-O-methyl-D-galactono-γ-lactone (5), which was obtained by an intramolecular WALDEN inversion of 3,5,6-tri-O-benzyl-4-O-mesyl-2-O-methyl-D-glucono-N-methylamide (4). Compound 5 shows the correct steric arrangement of the asymmetric centres with respect to noviose. Successive transformations (6-10) led to the synthesis of noviose and finally (9-14) to methyl 3-O-carbamoyl-α-novioside, which was identical with the substance obtained by acid catalysed methanolysis of the antibiotic novobiocin.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19640470207
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