Synthesis and Conformational Analysis of Macrocyclic Dilactones Mimicking the Pharmacophore of Aplysiatoxin

✍ Scribed by Henner Knust; Reinhard W. Hoffmann

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 373 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390151

✦ Synopsis

Abstract

A small number of macrocyclic dilactones of type 3, i.e., 9, 10, 11, and epi‐11, comprising a 3,4‐dihydroxypentanoic acid unit, the pharmacophore of aplysiatoxin, and a conformationally preorganized ω‐hydroxynonanoic acid unit were synthesized. Conformational analysis – based on ^2^J and ^3^J NMR coupling constants – of the dihydroxypentanoyl part of these macro‐dilactones indicates the extent to which a conformation induction across the macro‐dilactone ring occurs from the stereogenic centres implemented in the ω‐hydroxynonanoic acid part.