Stereochemical issues related to the synthesis and reactivity of pyrazino [2',1'-5,1] pyrrolo[2,3-b]indole- 1,4-diones

Tetrahedron Asymmetry

Volumn 9, Issue 6, 1998, Pages 967-981

  Caballero, Esmeralda ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PIPERAZINEDIONE;

ACYLATION; ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0032571455     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00068-8     Document Type: Article

References (35)

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2. Fructigenine B has been isolated both from Penicillium fructigenum and Penicillium verrucosum, and hence the alternative name verrucofortine. See: Hodge, R. P.; Harris, C. M.; Harris, T. M. J. Nat. Prod. 1988, 51, 66.
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4. (b) Takase, S.; Kavai, Y.; Uchida, I.; Tanaka, H.; Akoi, H. Tetrahedron 1985, 41, 3037.
5. (c) Laws, I.; Mantle, P. G. Phytochemistry 1985, 24, 1395.
6. A stereoisomer of amauromine has also been isolated from natural sources. See: de Guzmán, F. S.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1992, 55, 931.
7. Isolation and structural determination: Safe, S.; Taylor, A. J. Chem. Soc., Perkin Trans. 1 1972, 472 and references therein. For a commentary on the total synthesis of the sporidesmins, see: Anand, N.; Bindra, J. S.; Ranganathan, S. Art in Organic Synthesis (2nd Edition), John Wiley & Sons, 1988, p. 330.
8. Isolation and structural determination: Safe, S.; Taylor, A. J. Chem. Soc., Perkin Trans. 1 1972, 472 and references therein. For a commentary on the total synthesis of the sporidesmins, see: Anand, N.; Bindra, J. S.; Ranganathan, S. Art in Organic Synthesis (2nd Edition), John Wiley & Sons, 1988, p. 330.
9. Hochlowski, J. E.; Mullaly, M. M.; Spanton, S. G.; Whittern, D. N.; Hill, P.; McAlpine, J. B. J. Antibiot. 1993, 46, 380.
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12. (b) Maes, C. M.; Potgieter, M.; Steyn, P. S. J. Chem. Soc., Perkin Trans. 1 1986, 861. For the recent isolation of a related natural product with cytotoxic properties, see: Varoglu, M.; Corbett, T. H.; Valeriote, F. A.; Crews, P. J. Org. Chem. 1997, 62, 7078.
13. (a) Müllbacher, A.; Waring, P.; Tiwari-Palni, U.; Eichner, R. D. Mol. Immunol. 1986, 23, 231.
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16. Hino, T.; Nakagawa, M. In The Alkaloids, Brossi, A. (ed.), Vol. 34, Pergamon Press, 1988, p. 1.
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21. Elimination of the N-Boc protection under thermal conditions: Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19.
22. Compounds 5 and 6 have been prepared through an alternative route, although no spectral data were given. See: Nakashima, R.; Slater, G. T. Can. J. Chem. 1969, 47, 2069. Compound 5a has also been isolated from natural sources (see Ref. 25, for instance).
23. Longer treatment (ca. 15 min) leads to reversal of the cyclization by ring opening.
24. Partial reversion to 1 was observed during the acetylation reactions, leading to the isolation of 1a (28%) and 1b (24%).
25. Reviews on diketopiperazines: Natural products containing the diketopiperazine unit: (a) Johne, S.; Gröger, D. Pharmazie 1977, 32, 1.
26. (b) Sammes, P. G. Progress Chem. Nat. Prod. 1975, 32, 51. Conformational aspects: Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1978, 87, 627. Synthesis and reactivity: Rajappa, S.; Natekar, M. V. Adv. Heterocycl. Chem. 1993, 57, 187.
27. (b) Sammes, P. G. Progress Chem. Nat. Prod. 1975, 32, 51. Conformational aspects: Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1978, 87, 627. Synthesis and reactivity: Rajappa, S.; Natekar, M. V. Adv. Heterocycl. Chem. 1993, 57, 187.
28. (b) Sammes, P. G. Progress Chem. Nat. Prod. 1975, 32, 51. Conformational aspects: Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1978, 87, 627. Synthesis and reactivity: Rajappa, S.; Natekar, M. V. Adv. Heterocycl. Chem. 1993, 57, 187.
29. Rajappa, S.; Advani, B. G. Tetrahedron 1973, 29, 1299.
30. The higher degree of epimerization upon heating 11 with benzoyl chloride is probably related to the presence of HCl in the reaction medium, a stronger acid then the AcOH liberated in the reactions with acetic anhydride.
31. The alternative boat conformation is prevented by steric interactions between the pseudoaxial methyl group and the adjacent pentagonal ring. (matrix presented)
32. 3) ppm. (matrix presented)
33. Although the crude dipeptides thus obtained are virtually pure, they may contain traces of acid, which can only be completely eliminated by chromatography. Their presence causes epimerization of the tryptophan stereocenter of the diketopiperazines during the pyrolysis step. For example, under these conditions 4b led to 50% of 6b and 50% of 5a.
34. Hamasaki, T.: Nagayama, K.; Hatsuda, Y. Agr. Biol. Chem. 1976, 40, 2487.
35. There is a remarkable difference between the [α] values of compounds 5 and 6 when measured in ethanol and in DMSO. See, for instance, our polarimetric data for compound 5a, which are of opposite signs in these two solvents.