Antimony-templated macrolactamization of tetraamino esters. Facile synthesis of macrocyclic spermine alkaloids, (±)-buchnerine, (±)-verbacine, (±)-verbaskine, and (±)-verbascenine

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1569-1570

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

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BERBASCENINE; BUCHNERINE; SPERMINE DERIVATIVE; UNCLASSIFIED DRUG; VERBACINE; VERBASKINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029919944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953541a     Document Type: Article

References (33)

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4. 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. (a) Yamamoto, H.; Maruoka, K. J. Am. Chem. Soc. 1981, 103, 6133. (b) Ishihara, K.; Kuroki, Y.; Yamamoto, H. Synlett 1995, 41.
5. 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. (a) Yamamoto, H.; Maruoka, K. J. Am. Chem. Soc. 1981, 103, 6133. (b) Ishihara, K.; Kuroki, Y.; Yamamoto, H. Synlett 1995, 41.
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23. 2a
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28. 9 was isolated in 1982 by Hesse and his colleagues from Verbascum phoeniceum L. and Verbascum nigrum L. (a) Seifert, K.; Johne, S.; Hesse, M. Helv. Chim. Acta 1982, 65, 2540. For total synthesis of (±)-9. see: (b) Wasserman, H. H.; Robinson, R. P. Tetrahedron Lett. 1983, 24, 3669.
29. Although similar results were given in the use of methylboronic acid and phenylboronic acid, regioselectivity and chemical yield were best when (3,5-bis(trifluoromethyl)phenyl)boronic acid was used.
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