Design of the Synthesis of Steroidal 1,3,5(10),9(11)-Tetraenes via Isomerization of 1,3,5(10),8-Isomers - effect of the Solvent System

References

• Stephan , E. , Zen , R. , Authier , L. and Jaoven , G. 1995 . Steroids , 60 : 809
   PubMedGoogle Scholar
• Schwarz , S. , Ring , S. , Weber , G. , Teichmueller , G. , Palme , H.-J. , Pfeiffer , C. , Undetusch , B. , Erhart , B. and Grawe , D. 1994 . Tetrahedron , 50 : 10709
   Web of Science ®Google Scholar
• Kasch , H. and Ponsold , K. Ger. (East) DD 205169 . 1983 .
   Google Scholar
• Kasch , H. and Ponsold , K. 1984 . J. Prakt. Chem. , 326 : 941
   Google Scholar
• Smith , H. Brit. 1024912 . 1966 .
   Google Scholar
• Posner , G. H. , Mallamo , J. P. and Black , A. Y. 1981 . Tetrahedron , 37 : 3921
   Google Scholar
• Groen-Piotrowska , E. M. and Groen , M. B. 1993 . Recl. Trav. Chim. Pays-Bas , 112 : 627
   Google Scholar
• Baier , H. , Duerner , G. and Quinkert , G. 1985 . Helv. Chim. Acta , 68 : 1054
   Google Scholar
• Mikami , K. , Takahashi , K. , Nakai , T. and Uchimaru , T . 1994 . J. Am. Chem. Soc. , 116 : 10948
   Google Scholar
• Cohen , N. US 3971809 . 1976 .
   Google Scholar
• Chem. Abstr. , 85 177782
   Google Scholar
• Cohen , N. US 3933870 . 1976 .
   Google Scholar
• Chem. Abstr. , 84 135942
   Google Scholar
• Hughes , G. A. and Smith , H. US 3391170 . 1968 .
   Google Scholar
• Zhou , L.-M. 1988 . Ph.D Thesis School of Pharmaceutical Sciences, Beijing Medical University . An alternative synthetic approach to desogestrel and its derivatives from 1a developed in our group
   Google Scholar
• Liu , L.-G. , Zhang , T. and Li , Z.-S. 1996 . Tetrahedron , 52 : 4495
   Google Scholar
• Liu , L.-G. , Su , X.-D. and Li , Z.-S. 1995 . Synth. Commun. , 25 : 3113
   Web of Science ®Google Scholar
• Steroid Research Group, Shanghai Institute of Org. Chem. 1976 . Academia Sinica Huaxue Tongbao , 5 : 279
   Google Scholar
• Han , G. D. , Yang , G. Z. , Zheng , D. K. , Lu , G. S. , Xu , H. Q. , Zhang , Z. M. and Niu , S. L. 1980 . Yaoxue Xuebao , 15 : 169
   Google Scholar
• Liu , L.-G. , Li , Z.-S. , Su , X.-D. and Gao , H.-W. CN 1063107 . 1992 .
   Google Scholar
• Hainaut , D. and Bucourt , R. 1978 . Bull. Soc. Chim. Fr. , : 126 Pt. 2
   Google Scholar
• Chem. Abstr. , 89 197785 However the calculation by using Sybyl and AM1 methods in our group indicated 1,3,5(10), 8-isomers (1a, 1b and 1c, R=COCH3) were thermodynamically more stable than the corresponding 9(11)-isomers (2a-c) in gas-phase
   Google Scholar
• Weast , R. C. , Astle , M. J. and Beyer , W. H. , eds. 1986–1987 . CRC Handbook of Chemistry and Physics, , 67th ed. , E49 – E52 . Boca Raton, Florida : CRC Press Inc. . E70–74
   Google Scholar
• Lowry , T. H. and Richardson , K. S. 1976 . Mechanism and Theory in Organic Chemistry , 84 – 90 . New York : Harper & Row, Publishers . Hagerstown, San Francisco, London
   Google Scholar
• An alternative procedure of the transformation of 17-alcohol 2a to 3 and 4 was reported recently.1b
   Google Scholar