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

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

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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References

1a Corbaz R. Ettlinger L. Gäumann E. Keller-Schierlein W. Kradolfer F. Neipp L. Prelog V. Zähner H. Helv. Chim. Acta 1955, 38: 1445

1b Dominguez J. Dunitz JD. Gerlach H. Prelog V. Helv. Chim. Acta 1962, 45: 129

1c Beck J. Gerlach H. Prelog V. Voser V. Helv. Chim. Acta 1962, 45: 620

1d Ando K. Oishi H. Hirano S. Okutomi T. Suzuki K. Okazaki H. Sawada M. Sagawa T. J. Antibiot. 1971, 24: 347

1e Ando K. Murakami Y. Nawata Y. J. Antibiot. 1971, 24: 418

1f Keller-Schierlein W. Gerlach H. Seibl J. Antimicrob. Agents Chemother. (1966) 1967, 644

1g Keller-Schierlein W. Gerlach H. Fortschr. Chem. Org. Naturst. 1967, 26: 161

1h Gerlach H. Hütter R. Keller-Schierlein W. Seibl J. Zähner H. Helv. Chim. Acta 1967, 50: 1782

2a Zizka Z. Folia Microbiol. 1998, 43: 7

2b Tanouchi Y. Shichi H. Immunology 1988, 63: 471

2c Mori A. Kaminuma O. Ogawa K. Nakata A. Egan RW. Akiyama K. Okudaira H. J. Allergy Clin. Immunol. 2000, 106: S58

3a Gerlach H. Oertle K. Thalmann A. Servi S. Helv. Chim. Acta 1975, 58: 2036

3b Gombos J. Haslinger E. Zak H. Schmidt U. Tetrahedron Lett. 1975, 3391

3c Fleming I. Ghosh SK. J. Chem. Soc., Perkin Trans. 1 1998, 2733

3d Fleming I. Ghosh SK. In Studies in Natural Products Chemistry Vol. 18: . Elsevier; Amsterdam: 1996. p.229 ; and references cited therein

3e Wu Y. Sun Y.-P. Org. Lett. 2006, 8: 2831 ; and references cited therein

3f Zhou Y. Xu Q. Zhai H. Tetrahedron Lett. 2008, 49: 5271

4a Hanadate T. Kiyota H. Oritani T. Biosci., Biotechnol., Biochem. 2001, 65: 2118

4b Hanadate T. Kiyota H. Oritani T. Biosci., Biotechnol., Biochem. 2000, 64: 1671

4c Takai K. Hanadate T. Yamada T. Kuwahara S. Kiyota H. Tetrahedron 2011, 67: 7066

5a Coutable L. Adil K. Saluzzo C. Tetrahedron 2008, 64: 11296

5b Coutable L. Saluzzo C. Synthesis 2008, 3389

6a Abe M. Kiyota H. Adachi M. Oritani T. Synlett 1996, 777

6b Kiyota H. Abe M. Ono Y. Oritani T. Synlett 1996, 1093

7 Uneyama K. Organofluorine Chemistry Blackwell Publishing; Oxford: 2006.

8 Nickson TE. J. Org. Chem. 1988, 53: 3870

9 Palacios F. Pascual S. Oyarzabal J. Ochoa de Retana AM. Org. Lett. 2002, 4: 769

10 Kuno A. Sugiyama Y. Katsuta K. Sakai H. Takasugi H. Chem. Pharm. Bull. 1992, 40: 2423

11 Kubota T. Yamamoto M. Tetrahedron Lett. 1992, 33: 2603

12a Rychnovsky SD. Bartlett PA. J. Am. Chem. Soc. 1981, 103: 3963

12b Marek I. Lefrançis J.-M. Normant J.-F. Tetrahedron Lett. 1992, 33: 1747

13 Ullmann J. Hanak M. Synthesis 1989, 685

14 Ramachandran PV. Jennings MP. Org. Lett. 2001, 3: 3789

15 Tokuyama H. Yokoshima S. Yamashita T. Fukuyama T. Tetrahedron Lett. 1998, 39: 3189

16 Prakash GKS. Krishnamurti R. Olah GA. J. Am. Chem. Soc. 1989, 111: 2226