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Synthetic studies on bicyclomycin I synthesis of 1-allyl and benzoyl-8,10-dimethyl-6-methoxy-5-methylene-8,10-diaza-2-oxabicyclo[4.2.2]Decane-7,9-dione, which have the bicyclo ring system found in antibiotic bicyclomycin

✍ Scribed by Shin-ichi Nakatsuka; Kumi Yoshida; Toshio Goto


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
238 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis


Regiospecific cyclization of the alcohol &into the bicyclo[ 4.2.21 compound g was achieved via selective activation of the secondary methoxy group and subsequent acid treatment.

A side-chain was introduced at the bridge-head position, thus making up the bicyclomycin skeleton.

Bicyclomycin, which is produced by Streptomyces sapporonensis' and S. aizunensis, 2 possesses unique antibacterial activities.