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Synthesis of ( S )‐Nonacosan‐10‐ol, the Major Component of Tubular Plant Wax Crystals
Author(s) -
Dommisse Aarnoud,
Wirtz Jennifer,
Koch Kerstin,
Barthlott Wilhelm,
Kolter Thomas
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700262
Subject(s) - chemistry , wax , elongation , organic chemistry , metathesis , enantiomer , component (thermodynamics) , stereochemistry , polymer chemistry , polymerization , polymer , materials science , thermodynamics , physics , metallurgy , ultimate tensile strength
( S )‐Nonacosan‐10‐ol [( + )‐Ginnol] is the main component of the tubular wax aggregates, which are found on many plant leaves. To investigate the role of this lipid for the formation of super hydrophobic self‐cleaning plant surfaces, both enantiomers of the title compound were prepared in six steps. Key steps are the resolution of the allylation product of decanal with ( R )‐ O ‐methylmandelic acid, and a chain elongation by cross metathesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)