Total synthesis without protection: Three-step synthesis of optically active clavicipitic acids by a biomimetic route

European Journal of Organic Chemistry

Volumn , Issue 6, 2004, Pages 1244-1253

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

^a TOHO UNIVERSITY   (Japan)

Author keywords

Clavicipitic acids; Heck reaction; Protecting groups; Total synthesis; Tryptophan

Indexed keywords

2 METHYL 3 BUTEN 2 OL; 4 BROMOINDOLE; 4 BROMOTRYPTOPHAN; 4 VINYLTRYPTOPHAN; CLAVICIPITIC ACID DERIVATIVE; DEXTRO SERINE; ERGOT ALKALOID; INDOLE DERIVATIVE; METHYL GROUP; PALLADIUM; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ALKALINITY; ALLYLATION; ARTICLE; BIOMIMETICS; CATALYSIS; CATALYST; CYCLIZATION; DEPROTECTION REACTION; HECK REACTION; PH MEASUREMENT;

EID: 4544248742     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300603     Document Type: Article

References (45)

1. Part of this work has previously been published as a communication; see: Y. Yokoyama, H. Hikawa, M. Mitsuhashi, A. Uyama, Y. Murakami, Tetrahedron Letters 1999, 40, 7803-7806.
2. H. G. Floss, Tetrahedron 1976, 32, 873-912.
3. G. M. Coppola, H. F. Schuster, Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids, John Wiley & Sons: New York, 1987.
4. G. C. Barrett, in: Chemistry and Biochemistry of Amino Acids (Eds.: G. C. Barrett), Chapman and Hall: London, 1985; pp. 354-375.
5. H. R. Snyder, J. A. MacDonald, J. Am. Chem. Soc. 1955, 77, 1257-1259.
6. Although we have reported that the reaction of 4-bromoindole (7) with N-acetyldehydroalanine (11) did not proceed, reexamination of this experiment showed that in fact, the reaction gave N-acetyl-4-bromotryptophan (12b); see ref. [2].
7. K. Irie, A. Ishida, T. Nakamura, T. Ohishi, Chem. Pharm. Bull. 1984, 32, 2126-2139.
8. Pure acid dl-12b was obtained after chromatography with neutralized silica gel (hexane/EtOAc, 1:2) in 71% yield (see Exp. Sect.).
9. Y. Yokoyama, T. Matsumoto, Y. Murakami, J. Org. Chem. 1995, 60, 1486-1487.
10. [10a] H. Shinohara, T. Fukuda, M. Iwao, Tetrahedron 1999, 55, 10989-11000.
11. [10b] M. Iwao, F. Ishibashi, Tetrahedron 1997, 53, 51-58.
12. [10c] M. Somei, S. Hamamoto, K. Nakagawa, F. Yamada, T. Ohta, Heterocycles 1994, 37, 719-24.
13. [10d] A. Boyles, D. E. Nichols, J. Org. Chem. 1988, 53, 5128-30.
14. [10e] M. Matsumoto, H. Kobayashi, N. Watanabe, Heterocycles 1987, 26, 1197-202.
15. [10f] A. P. Kozikowski, M. N. Greco, J. Org. Chem. 1984, 49, 2310-2314.
16. [10g] H. Muratake, T. Takahashi, M. Natsume, Heterocycles 1983, 20, 1963-8.
17. T. Jeffery, Tetrahedron Lett. 1994, 35, 3051-3054.
18. J. S. Merola, H. Stetlzer, in: Aqueous-Phase Organometaallic Catalysis: Concepts and Application) (Eds.: B. Cornils, W. A. Hermann), Wiley-VCH: Weinheim, 1998; pp. 58-89.
19. N. A. Bumagin, K. V. Nikitin, I. P. Beletskaya, J. Organomet. Chem. 1988, 358, 563-565.
20. Clavicipitic acids were isolated as an isomeric mixture, and the melting point of the mixture has been reported: C.-W. Robbers, H. Otsuka, H. G. Floss, J. Org. Chem. 1980, 45, 1117-1121.
21. [15a] D. E. Metzler, M. Ikawa, E. E. Snell, J. Am. Chem. Soc. 1954, 76, 648-652.
22. [15b] W. Weiner, J. Winkler, S. C. Zimmerman, W. Czarnik, R. Breslow, J. Am. Chem. Soc. 1985, 107, 4093-4094.
23. [15b] Y. Murakami, Y. Hisaeda, T. Miyajima, H. Sakata, J. Kikuchi, Chem. Lett. 1993, 645-648 and references are cited therein.
24. Y. Yokoyama, K. Osanai, M. Mitsuhasi, K. Kondo, Y. Murakami, Heterocycles 2002, 55, 653-659.
25. [17a] Y. Yokoyama, K. Kondo, M. Mitsuhashi, Y. Murakami, Tetrahedron Lett. 1996, 37, 9309-9312.
26. [17b] K. Osanai, Y. Yokoyama, K. Kondo, Y. Murakami, Chem. Pharm. Bull. 1999, 47, 1587-1590.
27. 2O. A similar reaction has also been reported: M. Nakagawa, Y. Torisawa, T. Hosoka, K. Tanabe, F. Tavet, M. Aikawa, T. Hino, Heterocycles 1993, 35, 1167-1170.
28. [19a] C. Balsamini, G. Diamantini, A. Duranti, G. Spadoni, A. Tontini, Synthesis 1995, 370-372.
29. [19b] G. Spadoni, C. Balsamini, A. Bedini, E. Duranti, A. Tontini, J. Heterocyclic Chem. 1992, 29, 305-309.
30. [19c] G. Tarizia, C. Balsamini, G. Spandoni, E. Duranti, Synthesis 1988, 514-517.
31. [20a] J. S. Yadav, S. Abraham, B. V. S. Rekky, G. Sabitha, Synthesis 2001, 2165-2169.
32. [20b] K. Manabe, N. Aoyama, S. Kobayashi, Adv. Synth. Catal. 2001, 343, 174-176.
33. [20c] P. Harrington, M. A. Kerr, Can. J. Chem. 1998, 76, 1256-1265.
34. H. Johnson, D. G. Crosby, J. Org. Chem. 1960, 25, 569-570.
35. Snyder also proposed the same intermediate 24, see ref.[5]
36. A. L. Casalnuovo, J. C. Calabrese, J. Am. Chem. Soc. 1990, 112, 4324-4330.
37. P. Brewster, F. Hiron, C. K. Ingold, P. A. D. S. Rao, Nature 1950, 166, 179-180.
38. Comprehensive review of the Heck reaction in aqueous media; I. P. Beletskaya, A. V. Cheprakow, chapter 6, in: Organic synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998; pp. 141-213.
39. [26a] S.-C. Yong, C.-W. Hung, J. Org. Chem. 1999, 64, 5000-5001.
40. [26b] M Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065-1078.
41. [26c] F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969.
42. N2′ mechanism, but rather via π-allyl-palladium complex 25 (Scheme 8).
43. H. Yokoyama, H. Hikawa, Y. Murakami, J. Chem. Soc., Perkin 1 2001, 1431-1434.
44. Somei and Yamada reported the synthesis of dl-6,7-secoagroclavine and dl-aurantioclavine without using any protective groups. [29a] M. Somei, F. Yamada, Chem. Pharm. Bull. 1984, 32, 5064-5065.
45. [29b] F. Yamada, Y. Makita, T. Suzuki, M. Somei, Chem. Pharm. Bull. 1985, 33, 2162-2163.