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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 21
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Original Articles

Stereospecific Synthesis of Steroidal 20,16-γ-Carbolactones

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Pages 4043-4057 | Received 15 May 1998, Published online: 16 Aug 2006

REFERENCES

  • Rahman , A. and Choudhary , M. I. 1997 . Nat. Prod. Rep. , 14 : 191 For a recent review see:
  • Fieser , L. F. and Fieser , M. 1959 . Steroids , 810 – 846 . New York, NY : Reinhold Publishing Corp. .
  • Basu , N. and Rastogi , R. P. 1967 . Phytochemistry , 6 : 1249
  • Shakirov , R. and Yunusov , M. S. 1990 . Nat. Prod. Rep. , 7 : 557
  • Kessar , S. V. , Rampal , A. L. and Gupta , Y. P. 1968 . Tetrahedron , 24 : 905 and references cited therein
  • Homan , R. and Krause , B. R. 1997 . Current Pharmacological Design , 3 : 29
  • Mazur , Y. , Danieli , N. and Sondheimer , F. 1960 . J. Am. Chem. Soc. , 82 : 5889
  • Epimerization of lactone 8 to 9 has been described in this reference
  • Oka , K. and Hara , S. 1978 . J. Org. Chem. , 43 : 4408
  • Barton , D. H. R. , Beckwith , A. L. J. and Goosen , A. 1965 . J. Chem. Soc. , : 181
  • González , A. G. , Francisco , C. G. , Barreira , R. F. and Lopez , E. S. 1971 . An. Quím. , 67 : 433 Vespertilin (1b):
  • 1971 . Chem. Abst. , 75 : 115890n
  • Chakravarty , A. K. , Das , B. and Pakrashi , S. C. 1982 . Phytochemistry , 21 : 2083 Solanolide (1c):
  • Nagaoka , T. , Yoshihara , T. and Sakamura , S. 1987 . Phytochemistry , 26 : 2113 See also Lycopersiconolide:
  • González , A. G. , Freire , R. , Francisco , C. G. , Salazar , J. A. and Suárez , E. 1973 . Tetrahedron , 29 : 1731 20S-hydroxyvespertilin:
  • Doller , D. and Gros , E. G. 1990 . Synth. Commun. , 20 : 3115 Addition reaction of the enolate of methyl propionate or propionic acid to the C-17 keto group does not proceed as cleanly as with the t-butyl propionate enolate
  • Schnuff , N. R. and Trost , B. M. 1983 . J. Org. Chem. , 48 : 1404
  • Kobayashi , N. , Hisada , A. and Shimada , K. 1993 . J. Chem. Soc. Perkin Trans. I , : 31 For assignment of Z stereochemistry, see:
  • Clark , I. M. , Denney , W. A. , Jones , B. R. H. , Meakins , G. D. , Pendlebury , A. and Pinhey , J. T. 1972 . J. Chem. Soc. Perkin Trans. , I : 2765
  • Brown , H. C. and McFarlin , R. F. 1958 . J. Am. Chem. Soc. , 80 : 5372
  • Aristoff , P. A. , Johnson , P. D. and Harrison , A. W. 1985 . J. Am. Chem. Soc. , 107 : 7967
  • Sato , Y. and Ikekawa , N. 1961 . J. Org. Chem. , 26 : 5058
  • Lactone 1a was also obtained from the unprotected 3β-hydroxy analog of enone 14 by treatment with t-butyl isocyanide/TiCl4,15 which afforded the corresponding nitrile analog to 15. The remaining steps were as described for the 3β-OTBDMS steroid
  • Ito , Y. , Kato , H. , Imai , H. and Saegasa , T. 1982 . J. Am. Chem. Soc. , 104 : 6449

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