Syntheses of Prekinamycin and a Tetracyclic Quinone from Common Synthetic Intermediates

✍ Scribed by Shingo Kimura; Satoshi Kobayashi; Takuya Kumamoto; Aki Akagi; Naomi Sato; Tsutomu Ishikawa

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 246 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000296

✦ Synopsis

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.