Synthesis of Protected 4-Deoxyaklanonic Acid via Naphthalene-substituted Oligoketides

✍ Scribed by Krohn, Karsten ;Schäfer, Gisbert

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 704 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619960217

✦ Synopsis

Abstract

Ketide side chains (C~4~) were attached to the naphthoquinone 3 by reaction with the dienes 4 or 14 followed by Baker‐Venkataraman rearrangement of esters 8 and 17 to attach the second protected β‐diketo side chain. Linear anellations of the corresponding naphthoquinone precursors 9 and 17 to the 4‐deoxyaklanonic acids 10 and 18a, respectively, were effected in a base‐catalyzed cascade of reactions (e.g. only three operations from 3 to 18a).