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Syntheses of Prekinamycin and a Tetracyclic Quinone from Common Synthetic Intermediates
Authors:Shingo Kimura  Satoshi Kobayashi  Takuya Kumamoto  Aki Akagi  Naomi Sato  Tsutomu Ishikawa
Institution:1. Graduate School of Pharmaceutical Sciences, Chiba University, 1‐33 Yayoi‐cho, Inage‐ku, Chiba 263‐8522, Japan;2. Present address: Faculty of Pharmaceutical Sciences, Musashino University, 1‐1‐20 Shinmachi, Nishitokyo, Tokyo 202‐8585, Japan (phone/fax: +81‐42‐468‐9278).
Abstract:Towards total synthesis of a series of kinamycin and related antibiotics via common synthetic intermediates, total synthesis of prekinamycin was achieved via Suzuki coupling of naphthaleneboronic acid and bromobenzene derivative, intramolecular Friedel? Crafts reaction of 2‐(naphthalen‐2‐yl)benzoic acid, and diazotization in ten steps from 3,5‐dimethylphenol. Synthetic studies towards kinamycin antibiotics was also examined, and the tetracyclic quinone core for kinamycins was synthesized. Palladium‐catalyzed site‐selective hydroxylation of a benzoic acid derivative with the AB‐D ring part was successfully applied to the selective D‐ring functionalizations.
Keywords:Kinamycins  Prekinamycin  Suzuki coupling  Friedel?Crafts reaction  Hydroxylation
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