References
- Castedo , L. , Granja , J. R. and Mouriño , A. 1985 . Tetrahedron Lett. , 26 : 4959
- Castedo , L. , Granja , J. R. , Mouriño , A. and Pumar , M. C. 1987 . Synth. Commun. , 17 : 251
- Mikami , K. , Kawamoto , K. and Nakai , T. 1985 . Tetrahedron Lett. , 26 : 5799 for related work, see:
- Nakai , T. and Mikami , K. 1986 . Chem. Rev. , 86 : 885 For a review on [2,3]-Wittig sigmatropic rearrangements, see:
- Norman , A. W. 1979 . “Vitamin D, the Calcium Homeostatic Steroid Hormone” , New York : Academic .
- Zhou , J. , Norman , A. W. , Lubbert , E. D. , Collins , E. D. , Uskokovic , M. R. and Koeffler , H. P. 1987 . Blood , 74 : 82 The vitamin D analogue with a double bond bewteen C16 and C17 has very slight calcemic effects
- Redpath , J. and Zeelen , F. 1983 . Chem. Soc. Rev. , 12 : 75 For several approaches to introduce the steroid C16-C17 double bond, see:
- Schmuff , N. R. and Trost , B. M. 1983 . J. Org. Chem. , 48 : 1404
- Mikami , K. , Kawamoto , K. and Nakai , T. 1985 . Tetrahedron Lett. , 26 : 5799
- Koreeda , M. and Ricca , D. J. 1986 . J. Org. Chem. , 51 : 4096
- °Compound 1 was obtained from commercially available estrone by protection (TBDMSCI, imidazole, DMF, 99%), Wittig olefination (Ph3P+CH2CH3Br−, KOt-Bu, THF, 95%), and hydroxylation (SeO2, t-BuOOH, CH2Cl2, 89%).1
- Patridge , J. J. , Faber , S. and Uskokovic , M. R. 1974 . Helv. Chim. Acta. , 57 : 2036
- Trost , B. M. and Matsumura , Y. 1977 . J. Org. Chem. , 42 : 2036
- Sardina , F. J. , Mouriño , A. and Castedo , L. 1983 . Tetrahedron Lett. , 24 : 4477
- Sardina , F. J. , Mouriño , A. and Castedo , L. 1986 . J. Org. Chem. , 51 : 1264
- Middland , M. M. and Kwon , J. C. 1985 . Tetrahedron Lett. , 26 : 5017