Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus.
Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K(1) and K(2). Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.
Hakki
Zalihe
Z
Bio21 Molecular Science and Biotechnology Institute and School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Cao
Benjamin
B
Heskes
Allison M
AM
Goodger
Jason Q D
JQ
Woodrow
Ian E
IE
Williams
Spencer J
SJ
D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis*; D005052:Eucalyptus / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D039821:Monoterpenes / Q000138:chemical synthesis*; D009822:Oils, Volatile / Q000138:chemical synthesis; D018515:Plant Leaves / Q000737:chemistry
D003509:Cyclohexanecarboxylic Acids; D005960:Glucosides; D039821:Monoterpenes; D009822:Oils, Volatile; C543011:cuniloside B; C417929:cypellocarpin C