Novobiocin III . Die Glykosidsynthese des Novobiocins | Zendy

Vaterlaus B. P. | Zendy; Doebel K. | Zendy; Kiss J. | Zendy; Rachlin A. I. | Zendy; Spiegelberg H. | Zendy

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Novobiocin III . Die Glykosidsynthese des Novobiocins

Author(s) -

Vaterlaus B. P.,

Doebel K.,

Kiss J.,

Rachlin A. I.,

Spiegelberg H.

Publication year - 1964

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19640470208

Subject(s) - chemistry , novobiocin , acylation , hydrogenolysis , glycoside , stereochemistry , amine gas treating , chloride , organic chemistry , biochemistry , antibiotics , catalysis

The glycosidation of 4‐benzyloxy‐7‐hydroxy‐8‐methyl‐cumarin ( 2 ) with 2,3‐0‐carbonyl‐β‐noviosyl chloride ( 1 ) leading to the α‐glycoside ( 3 ) is described. This intermediate is transformed successively : (a) by hydrogenolysis ( 4 ), (b) introduction of an amine function ( 5 ) ( 6 ), (c) acylation with 4‐acetoxy‐3‐(isopent‐2′‐enyl)‐benzoyl chloride ( 10 ), (d) ammonolysis of 10 , into a mixture of novobiocin ( 11 ) and isonovo‐biocin ( 12 ), of which novobiocin was obtained by fractional crystallisation.

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