Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 10, Pages 3272-3276Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo010913r
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Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.
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