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