Download PDF by V. H. T. James, J. R. Pasqualini: Proceedings of the Fourth International Congress on Hormonal

By V. H. T. James, J. R. Pasqualini

ISBN-10: 0080196829

ISBN-13: 9780080196824

Proceedings of the Fourth overseas Congress on Hormonal Steroids includes plenary speeches and symposia from the Fourth overseas Congress on Hormonal Steroids held in Mexico urban in September 1974

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Extra resources for Proceedings of the Fourth International Congress on Hormonal Steroids. Mexico City, September 1974

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Sauer G. : Angew. Chem. Int. Ed. 10 (1971') 496-497. tion. 11. Rosenberger M. et al, forthcoming publication. 12. , Banner B. , Blount J. , Tsai M. : J. org. Chem. 38 (1973) 3229-3239. REFERENCES 13. , Banner B. , Eichel W. , Parrish D. 1. , Meier W. : thesis of 19-norsteroids see (a) Saucy G. and Cohen to be published. : in MTP International Review of Science, Series 14. (a) Hajos Z. G. and Parrish D. : J. org. Chem. One, Vol. 8, Steroids (Edited by W. F. , Hajos worths, London (1973), pp. 1-26.

It should be noted that this method might, itself, be an attractive one for the synthesis of estrone were it not for the inefficiency of the picolylethyla­ tion (46%). Nevertheless, for our purposes, it pro­ vided the crucial rotation data necessary to monitor the efficacy of our own attempts at asymmetric in­ duction. An important advance in the pyridine route to optically active estrone was achieved by the dis­ covery that treatment of 2-methylcyclopentane-l,3dione with \1] (Et 3 N-EtOAC) gave a nearly quantita­ tive yield of prochiral trione 24.

DANISHEFSKY and P. CAIN H20 2e" -H 2 0 Me 3 Fig. 1. of cyclohexenone 4. It is recognized that, in principle, a wide latitude of functionality may be encompassed in the formalism R. Included among these, is the possibility that R represents the CD system of a potential steroid appended via an ethano linkage. In that event, system 4 may be expanded to 5. It will be seen that 5 might be induced to undergo further aldolization, in a vinylogous sense, to give rise to 6. Compound 6 can be converted to 19norsteroids via chemical reduction, or to estrone itself by armotization.

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Proceedings of the Fourth International Congress on Hormonal Steroids. Mexico City, September 1974 by V. H. T. James, J. R. Pasqualini


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