Synthesis of Both Enantiomers
of ω-Trifluorononactic Acid, a New Analogue of Nonactin
Monomers

Kentaro Takai; Tadaatsu Hanadate; Shuichi Oi; Teiko Yamada; Shigefumi Kuwahara; Hiromasa Kiyota

doi:10.1055/s-0030-1260234

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Synthesis 2011(22): 3741-3748
DOI: 10.1055/s-0030-1260234

PAPER

Synthesis of Both Enantiomers of ω-Trifluorononactic Acid, a New Analogue of Nonactin Monomers

Kentaro Takai^a, Tadaatsu Hanadate^a, Shuichi Oi^b, Teiko Yamada^a, Shigefumi Kuwahara^a, Hiromasa Kiyota*^a
^a Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Sciences, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan
Fax: +81(22)7178785; e-Mail: kiyota@biochem.tohoku.ac.jp;
^b Environment Conservation Research Institute, Tohoku University, Japan

Weitere Informationen

Publikationsverlauf

Received 12 July 2011
Publikationsdatum:
21. September 2011 (online)

Abstract
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Abstract

Both (+)- and (-)-ω-trifluorononactic acid, a designed analogue of nonactic acid, were synthesized. The racemic acid, prepared by using cis-selective iodoetherification, was resolved as the corresponding (S)-O-acetylmandelates. The structure was determined by X-ray crystallographic analysis.

Key words

polynactins - antibiotics - ω-trifluorononactic acid - chiral resolution - total synthesis

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