Syntheses without protection: A three-step synthesis of optically active clavicipitic acid by utilizing biomimetic synthesis of 4-bromotryptophan

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7803-7806

  Yokoyama, Yuusaku ^a   Hikawa, Hidemasa ^a   Mitsuhashi, Masaharu ^a   Uyama, Aki ^a   Murakami, Yasuoki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Amino acid derivatives; Aqueous media; Cyclization; Heck reactions

Indexed keywords

ALLYL ALCOHOL; AMINO ACID DERIVATIVE; ERGOT ALKALOID; INDOLE DERIVATIVE; OXIDE; SERINE; TRYPTOPHAN;

AQUEOUS SOLUTION; ARTICLE; CYCLIZATION; OPTICAL ROTATION; SYNTHESIS;

EID: 0033615774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01620-2     Document Type: Article

References (17)

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2. 2. Barrett, G. C. In Chemistry and Biochemistry of Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: London, 1985; pp. 354-375.
3. 3. One of the most successful examples of synthetically useful reactions using free amino acids is deamination: Brewster, P.; Hiron, F.; Ingold, C. K.; Rao, P. A. D. S. Nature 1950, 166, 179-180. This reaction was elegantly applied to the synthesis of optically active ribose: Koga, K.; Taniguchi, M.; Yamada, S. Tetrahedron 1974, 30, 3547-3552.
4. 3. One of the most successful examples of synthetically useful reactions using free amino acids is deamination: Brewster, P.; Hiron, F.; Ingold, C. K.; Rao, P. A. D. S. Nature 1950, 166, 179-180. This reaction was elegantly applied to the synthesis of optically active ribose: Koga, K.; Taniguchi, M.; Yamada, S. Tetrahedron 1974, 30, 3547-3552.
5. 4. (a) Metzler, D. E.; Ikawa, M.; Snell, E. E. J. Am. Chem. Soc. 1954, 76, 648-652.
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8. 4c that a tryptophan-synthetase biomimetic reaction conducted in the presence of an N-alkylated pyridoxal quaternary salt and an optically active bilayer membrane consisting of synthetic peptide lipids gave quite unsatisfactory yields of tryptophan for synthetic purposes (3% yield, 35% ee).
9. 6. Snyder, H. R.; MacDonald, J. A. J. Am. Chem. Soc. 1955, 77, 1257-1259.
10. 2O. A similar reaction has been also reported: Nakagawa, M.; Torisawa, Y.; Hosoka, T.; Tanabe, K.; Tavet, F.; Aikawa, M.; Hino, T. Heterocycles 1993, 35, 1167-1170.
11. 2.
12. 9. Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J. Org. Chem. 1995, 60, 1486-1487.
13. 10. For a comprehensive review of Heck reaction in aqueous media, see: Beletskaya, I. P.; Cheprakow, A. V. In Organic Synthesis in Water; Grieco P. A., Ed.; Blackie Academic and Professional: London, 1998; Chap. 6, pp. 141-213.
14. 11. Merola, J. S.; Stelzer, H. In Aqueous-Phase Organometallic Catalysis: Concepts and Application; Cornnils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Wienheim, 1998; pp. 59-89.
15. 12. Since this reaction did not proceed without the palladium catalyst, a SN2′ type reaction mechanism was excluded in the formation of N-allyl derivative 13. Recently, Magari et al. reported the palladium catalyzed direct amination of 1,1-dimethylallyl alcohol with diethylamine: Magari, K.; Ishimura, Y.; Ooe, T.; Nagato, N. Nippon Kagakukaishi 1996, 250-255.
16. 13. The optical purities of cis and trans clavicipitic acid (4) were determined by HPLC after isolation of each isomer as methyl ester prepared by the reaction with diazomethane [Chiralpak AS (Daicel) hexane:iso-Pro-OH=50:1].
17. 14. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.