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Syntheses of 4-hydroxy-5-iodo-2,3-dimethoxy-6-methylbenzoic acid and 5-bromo-4-hydroxy-2,3-dimethoxy-6-methylbenzoic acid - aromatic constituents of the calichemicins

✍ Scribed by Kai van Laak; Hans-Dieter Scharf

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 431 KB
Volume: 45
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89497-7

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✦ Synopsis

Hy&o~-5-iodo-2J-dimdimethoxyd-methylbenzoic acid (1) and 5-bromo-4-hydroxy-2,3-dimethoxy-6-methylbenzoic acid (2) are the polysubstituted aromatic carboxylic aciakfoundin calichemicin antibiotics.' The title compounds are synthesized on preparative scale from readily available methyl 4-0-bensylorsellinate (3) in six steps without any chromatographic separation needed [(I) : 41 %I, (2) : 44 %, overall yield]. The calichemicins produced by Micromospora echinospora ssp. calichensis represent anew class of antitumor antibiotics witb an enediyne moiety. Tbe biological activity of the calichemicins is extraordinary, they ate approximately 4000-foldmoreactive againstmurinemmorsthanadriamycin 'a. Consequently they ate very interesting target mole-

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