Metal-Templated Macrolactamization of Triamino and Tetramino Esters. Facile Synthesis of Macrocyclic Spermidine and Spermine Alkaloids, (S)-(+)-Dihydroperiphylline, (±)-Buchnerine, (±)-Verbacine, (±)-Verbaskine, and (±)-Verbascenine

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 5, 1998, Pages 1221-1230

  Kuroki, Yoshichika ^b   Ishihara, Kazuaki ^a   Hanaki, Naoyuki ^a   Ohara, Suguru ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b DAIKIN INDUSTRIES LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000506128     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1221     Document Type: Article

References (43)

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2. Reviews: a) U. Bachrach. "Function of Naturally Occurring Polyamines," Academic Press, New York (1973); b) M. Hesse and H. Schmid, "Macrocyclic Spermidine and Spermine Alkaloids," from Int. Rev. Sci., ed by H. D. Hey and K. Wiesner, Butterworth, London (1976), Series II, Vol. 9. p. 265: c) M. M. Badawi, K. Bernauer, P. Van den Broek, D. Groger, A. Guggisberg, S. Johne, I. Kompis, F. Schneider, H.-J. Veith, M. Hesse, and H. Schmid, Pure Appl. Chem., 33, 81 (1973).
3. Reviews: a) U. Bachrach. "Function of Naturally Occurring Polyamines," Academic Press, New York (1973); b) M. Hesse and H. Schmid, "Macrocyclic Spermidine and Spermine Alkaloids," from Int. Rev. Sci., ed by H. D. Hey and K. Wiesner, Butterworth, London (1976), Series II, Vol. 9. p. 265: c) M. M. Badawi, K. Bernauer, P. Van den Broek, D. Groger, A. Guggisberg, S. Johne, I. Kompis, F. Schneider, H.-J. Veith, M. Hesse, and H. Schmid, Pure Appl. Chem., 33, 81 (1973).
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22. We previously described that the use of boron-templated cyclization of triamino esters with tris (dimethylamino)borane is highly efficient as a key step in the total synthesis of macrocyclic spermidine alkaloids containing 13-members. H. Yamamoto and K. Maruoka, J. Am. Chem. Soc., 103, 6133 (1981).
23. Part of this work has been published as preliminary communications: a) K. Ishihara, Y. Kuroki, and H. Yamamoto, Synlett, 1995, 41; b) K. Ishihara, Y. Kuroki, N. Hanaki, S. Ohara, and H. Yamamoto, J. Am. Chem. Soc., 118, 1569 (1996).
24. Part of this work has been published as preliminary communications: a) K. Ishihara, Y. Kuroki, and H. Yamamoto, Synlett, 1995, 41; b) K. Ishihara, Y. Kuroki, N. Hanaki, S. Ohara, and H. Yamamoto, J. Am. Chem. Soc., 118, 1569 (1996).
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27. 3) for (S)-9 (>95% ee);
28. 3) for (R)-9 (> 98% ee).
29. 8)
30. T. Sakamoto, F. Shiga, A. Yasuhara, D. Uchiyama, Y. Kondo, and H. Yamanaka, Synthesis, 1992, 746.
31. Tris(dimethylamino)borane which has a tendency to form a tridentate complex was not appropriate for a macrolactamization of tetramino esters.
32. It has been known that triorganoantimony(III) compounds have the strong tendency to form multidentate complexes. J. S. Thayer, "Organometallic Chemistry," VCH Publishers, Inc., New York (1998), p. 56.
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34. 3 was isolated in 1995 by Drandarov from Verbascum pseudonobile Stoj. et Stef. (Scrophulariaceae). Unfortunately, it was found that 4 is not a natural substance, but an artifact produced from 3 by reaction with phosgene (carbonyl chloride) in the chloroform used as extractant. K. Drandarov, Tetrahedron Lett., 36, 617 (1995).
35. a) P. Ninova, A. Abdusamatov, and S. Yu. Yunusov, Khim. Prir. Soedin., 1971, 540;
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37. 5 was isolated in 1982 by Hesse and his colleagues from Verbascum phoeniceum L. and Verbascum nigrum L. a) K. Seifert, S. Johne, and M. Hesse, Helv. Chim. Acta, 65, 2540 (1982); For total synthesis of (±)-5, see: b) H. H. Wasserman and R. P. Robinson, Tetrahedron Lett., 24, 3669 (1983).
38. 5 was isolated in 1982 by Hesse and his colleagues from Verbascum phoeniceum L. and Verbascum nigrum L. a) K. Seifert, S. Johne, and M. Hesse, Helv. Chim. Acta, 65, 2540 (1982); For total synthesis of (±)-5, see: b) H. H. Wasserman and R. P. Robinson, Tetrahedron Lett., 24, 3669 (1983).
39. Although similar results were given in the use of methylboronic acid and phenylboronic acid, regioselectivity and chemical yield were best using 3,5-bis(trifluoromethyl)phenylboronic acid.
40. We failed in an attempt to construct a cyclic urea unit bridged at N-11 and N-15 regioselectively by treatment of 27 with triphosgene.
41. For reference on amidation reaction using triphenylantimony(V) dicarboxylate or triphenylstibine(V) oxide, see: a) R. Nomura, T. Wada, Y. Yamada, and H. Matsuda, Chem. Lett., 1986, 1901; b) R. Nomura, T. Nakano, Y. Yamada, and H. Matsuda, J. Org. Chem., 56, 4076 (1991).
42. For reference on amidation reaction using triphenylantimony(V) dicarboxylate or triphenylstibine(V) oxide, see: a) R. Nomura, T. Wada, Y. Yamada, and H. Matsuda, Chem. Lett., 1986, 1901; b) R. Nomura, T. Nakano, Y. Yamada, and H. Matsuda, J. Org. Chem., 56, 4076 (1991).
43. For a review on synthetic applications of organoantimony compounds, see: Y.-Z. Huang, Acc, Chem. Res., 25, 182 (1992).