Synthesis of (S)‐Nonacosan‐10‐ol, the Major Component of Tubular Plant Wax Crystals

European Journal of Organic Chemistry - Tập 2007 Số 21 - Trang 3508-3511 - 2007
Aarnoud Dommisse1, Jennifer Wirtz2, Kerstin Koch1, Wilhelm Barthlott1, Thomas Kolter2
1Nees Institute for Biodiversity of Plants, University of Bonn, Meckenheimer Allee 170, 53115 Bonn, Germany
2Kekulé-Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany

Tóm tắt

Abstract(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)

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Tài liệu tham khảo

10.1016/S0163-7827(02)00045-0

Jetter R., 2006, Biology of the Plant Cuticle

10.1515/znb-1968-0411

10.1111/j.1095-8339.1998.tb02529.x

10.1007/BF00199686

10.1007/s004250050096

10.1007/s004250100530

10.1002/ange.19941060324

10.1016/S0040-4020(98)00688-7

10.1246/cl.1994.1093

10.1021/ja00312a062

10.1002/ange.19891010425

10.1016/0040-4039(94)88412-9

10.1021/jo961129n

10.1021/jo962240w

10.1016/S0957-4166(00)00374-8

10.1021/jo0202233

10.1039/b411173g

10.1002/ange.200504432

10.1002/ejoc.200500833

10.1021/ja993063u

K. Koch A. Dommisse W. Barthlott Cryst. Growth Des.2006 6 2571–2578