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Synthesis 2011(22): 3741-3748  
DOI: 10.1055/s-0030-1260234
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Kentaro Takaia, Tadaatsu Hanadatea, Shuichi Oib, Teiko Yamadaa, Shigefumi Kuwaharaa, 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
Further Information

Publication History

Received 12 July 2011
Publication Date:
21 September 2011 (online)

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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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