Steroids Related to the Diterpenoid Tumour Inhibitor Aphidicolin

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James R. Hanson, Peter B. Hitchcock and Cavit Uyanik


Abstract

The syntheses of 2α,17β-dihydroxy-2β-hydroxymethyl-A-nor-5α-androstane, 3β,17β-dihydroxy-3α-hydroxymethyl-5α-androstane and 3β,17α-dihydroxy-3α-hydroxymethyl-5α,13α-androstane are described, and the stereochemistry of osmylation of a 3-methylene-5α-androstane is established by X-ray crystallography.


References

  1. W. Dalziel, B. Hesp, K. M. Stevenson and J. A. J. Jarvis, J. Chem. Soc., Perkin Trans. 1, 1973, 2841 RSC.
  2. S. Ikegami, T. Taguchi and M. Ohashi, Nature (London), 1978, 275, 458 CAS.
  3. S. Hiranuma, T. Shimizu, H. Yoshioka, K. Ono, H. Nakane and T. Takahashi, Chem. Pharm. Bull. Jpn., 1978, 35, 1641 Search PubMed.
  4. K. Ono, Y. Iwata and H. Nakane, Biomed. Pharmacother., 1983, 37, 27 CAS.
  5. L. Arabshi, N. Brown, N. Khan and G. Wright, Nucleic Acid Res., 1988, 16, 5107 Search PubMed.
  6. J. A. Boynton and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1995, 2189 RSC.
  7. T. Rull and G. Ourisson, Bull. Soc. Chim., Fr., 1958, 1573 CAS.
  8. M. Minato, K. Yamamoto and J. Tsuji, J. Org. Chem., 1990, 55, 766 CrossRef.
  9. J. Kalvado and H. Kaufman, J. Chem. Soc., Chem. Commun., 1976, 209 RSC.
  10. J. R. Billeter and K. Miescher, Helv. Chim. Acta, 1951, 34, 2052 CrossRef.
  11. T. Nambara, H. Hosoda and S. Goya, Chem. Pharm. Bull. Jpn., 1968, 16, 1266 Search PubMed.
  12. C. R. Johnson, B. D. Tait and A. S. Cieplak, J. Am. Chem. Soc., 1987, 109, 5875 CrossRef CAS.
  13. G. M. Sheldrick, in SHELXS-86 Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1985 Search PubMed.
  14. G. M. Sheldrick, in SHELXL-93 Program for Crystal Structure Refinement, University of Göttingen, Germany, 1993 Search PubMed.
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