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Synthesis and Conformational Analysis of Macrocyclic Dilactones Mimicking the Pharmacophore of Aplysiatoxin
Author(s) -
Knust Henner,
Hoffmann Reinhard W.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390151
Subject(s) - chemistry , pharmacophore , stereocenter , stereochemistry , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis
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.