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0042541684
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doctoral thesis, University of Santiago de Compostela
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This paper is partially based on the doctoral thesis of Eva María Codesido, University of Santiago de Compostela, 2001.
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5 consists of a thermally induced antarafacial [1,7]-sigmatropic hydrogen shift from C19 to C9. For studies of the mechanism of this physiologically important transformation, see: (a) Havinga, E. Experientia 1973, 29, 1181-1192.
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0043042553
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note
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For convenience, steroid numbering is used.
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0043042551
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note
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The relative stereochemistry of 4 was determined by NOE experiments as in ref 3.
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The 15a/15b ratio was almost 1:1 after 48 and after 76 h. For an example of stereocontrolled RCM, see: Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378.
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0043042548
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H4-H5 coupling was close to zero.
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40
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0042541681
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin; Chapter 34.1
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