Selective Synthesis of Diastereomeric Fluorinated Octadeca-2,4-dienoates and Octadeca-2,4-dien-1-ols

Gergana S. Nikolova; Günter Haufe

doi:10.1055/s-2008-1032147

PAPER

Selective Synthesis of Diastereomeric Fluorinated Octadeca-2,4-dienoates and Octadeca-2,4-dien-1-ols

Gergana S. Nikolova, Günter Haufe*
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

A series of new methyl and ethyl octadeca-2,4-dienoates with one or two vinylic fluorine substituents in the 2- and/or 4-position and the corresponding alcohols were easily prepared by stereoselective Wittig-type reactions and subsequent reduction.

Key words

Wittig reactions - fluorine - dienes - fatty acids and alcohols - reductions

Volltext

Referenzen

References

<A NAME="RT14307SS-1">1</A> Laschewsky A. Ringsdorf H. Macromolecules 1988, 21: 1936

<A NAME="RT14307SS-2">2</A> Nikolova GS. Zhang L. Chen X. Chi L. Haufe G. Colloids Surf., A 2008, DOI: 10.1016/j.colsurfa.2007.11.013

<A NAME="RT14307SS-3">3</A> Oldendorf J. Haufe G. Eur. J. Org. Chem. 2006, 4463

<A NAME="RT14307SS-4A">4a</A> Steffens S. Höweler U. Jödicke T. Oldendorf J. Rudert R. Haufe G. Galla H.-J. Langmuir 2007, 23: 1880

<A NAME="RT14307SS-4B">4b</A> Steffens S. Oldendorf J. Haufe G. Galla H.-J. Langmuir 2006, 22: 1428

<A NAME="RT14307SS-4C">4c</A> Chen X. Wiehle S. Weygand M. Brezesinski G. Klenz U. Galla H.-J. Fuchs H. Haufe G. Chi L. J. Phys. Chem. B 2005, 109: 19866

<A NAME="RT14307SS-4D">4d</A> Chen X. Wiehle S. Chi L. Mück-Lichtenfeld C. Rudert R. Vollhardt D. Fuchs H. Haufe G. Langmuir 2005, 21: 3376

<A NAME="RT14307SS-5">5</A> Kobayashi Y. Morikawa T. Yoshizava A. Taguchi T. Tetrahedron Lett. 1981, 22: 5297

<A NAME="RT14307SS-6">6</A> Delgado A. Ruiz M. Camps F. Hospital S. Guerrero A. Chem. Phys. Lipids 1991, 59: 127

<A NAME="RT14307SS-7">7</A> Wrobel J. Millen J. Sredy J. Dietrich A. Gorham BJ. Malamas M. Kelly JM. Bauman JG. Harisson MC. Jones RL. Guinosso C. Sestanj K. J. Med. Chem. 1991, 34: 2504

<A NAME="RT14307SS-8">8</A> Cristau H.-J. Chem. Rev. 1994, 94: 1299

<A NAME="RT14307SS-9">9</A> Burton DJ. Chem. Rev. 1996, 96: 1641

<A NAME="RT14307SS-10">10</A> Kondo K. Cottens S. Schlosser M. Chem. Lett. 1984, 2149

<A NAME="RT14307SS-11">11</A> Camps F. Coll J. Fabrias G. Guerrero A. Tetrahedron 1984, 40: 2871

<A NAME="RT14307SS-12">12</A> Tellier F. Sauvêtre R. Tetrahedron Lett. 1993, 34: 5433

<A NAME="RT14307SS-13">13</A> Arimitsu S. Konno T. Gupton JT. Ishihara T. Yamanaka H. J. Fluorine Chem. 2006, 127: 1235

<A NAME="RT14307SS-14">14</A> Kitazume T. Ishikawa N. Chem. Lett. 1981, 1259

<A NAME="RT14307SS-15">15</A> Ishihara T. Kuroboshi M. Chem. Lett. 1987, 1145

<A NAME="RT14307SS-16">16</A> Shen Y. Zhou Y. J. Fluorine Chem. 1993, 61: 247

<A NAME="RT14307SS-17">17</A> Clemenceau D. Cousseau J. Tetrahedron Lett. 1993, 34: 6903

<A NAME="RT14307SS-18">18</A> Spahić B. Thu TTM. Schlosser M. Helv. Chim. Acta 1980, 63: 1236

<A NAME="RT14307SS-19">19</A> Etemad-Moghadam G. Seyden-Penne J. Bull. Soc. Chim. Fr. 1985, 448

<A NAME="RT14307SS-20">20</A> Thenappan A. Burton DJ. Tetrahedron Lett. 1989, 30: 5571

<A NAME="RT14307SS-21">21</A> Johnson WH. Wang SC. Stanley TM. Czerwinski RM. Almrud JJ. Poelarends GJ. Murzin AG. Whitman CP. Biochemistry 2004, 43: 10490

<A NAME="RT14307SS-22">22</A> Sano S. Teranishi R. Nagao Y. Tetrahedron Lett. 2002, 43: 9183

<A NAME="RT14307SS-23">23</A> Asato AE. Matsumoto H. Denny M. Liu RSH. J. Am. Chem. Soc. 1978, 100: 5957

<A NAME="RT14307SS-24">24</A> Pawson BA. Chain K.-K. DeNoble J. Han R.-JL. Piermattie V. Specian AC. Srisethnil S. J. Med. Chem. 1979, 22: 1059

<A NAME="RT14307SS-25A">25a</A> Yoshida M. Nagahara D. Fukuhara T. Yoneda N. Hara S. J. Chem. Soc., Perkin Trans. 1 2001, 2283

<A NAME="RT14307SS-25B">25b</A> Yoshida M. Hara S. Fukuhara T. Yoneda N. Tetrahedron Lett. 2000, 41: 3887

<A NAME="RT14307SS-26">26</A> Trost BM. Kunz RA. J. Am. Chem. Soc. 1975, 7152

<A NAME="RT14307SS-27">27</A> Solladié-Cavallo A. Koessler JL. J. Org. Chem. 1994, 59: 3240

<A NAME="RT14307SS-28">28</A> Thenappan A. Burton DJ. J. Org. Chem. 1990, 55: 2311

<A NAME="RT14307SS-29">29</A> Bargiggia F. Dos Santos S. Piva O. Synthesis 2002, 427

<A NAME="RT14307SS-30">30</A> Tsai H.-J. Thenappan A. Burton DJ. J. Org. Chem. 1994, 59: 7085