Elsevier

Tetrahedron Letters

Volume 41, Issue 26, 24 June 2000, Pages 5099-5101
Tetrahedron Letters

Facile synthesis of (+)-biotin via Fukuyama coupling reaction

https://doi.org/10.1016/S0040-4039(00)00781-4Get rights and content

Abstract

Treatment of a thiolactone 2 with a zinc reagent 3 in the presence of PdCl2(PPh3)2 (10 mol%) allowed installation of a C-2 side chain of (+)-biotin in a highly efficient manner, which enabled synthesis of (+)-biotin in three steps from 2.

References (14)

  • (a) Mistry, P. S.; Dakshinamurti, K. Vitam. Horm. 1964, 22, 1. (b) Coggeshall, C. J.; Heggers, P. J.; Robson, C. M.;...
  • For a review, see: Clercq, P. J. D. Chem. Rev. 1997, 97,...
  • (a) Goldberg, M. W.; Sternbach, L. H. US Patent 2,489,232, Nov. 22, 1949; Chem Abstr. 1951, 45, 184b. (b) Goldberg, M....
  • Isaka, I.; Kubo, K.; Takashima, M.; Murakami, M. Yakugaku Zasshi 1968, 88,...
  • Holick, W.; Pauling, H.; Cottong, N. A. European Patent Appl. EP 0 154 225 A2, Feb. 14, 1985; Chem. Abstr. 1986, 104,...
  • Ohashi, N.; Ikeda, T.; Shimago, K.; Takahashi, T.; Ishizumi, K. European Patent Appl. EP 84,377, Jul. 27, 1983; Chem...
  • Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39,...
There are more references available in the full text version of this article.

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