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A catalytic and stoichiometric approach to the synthesis of the steroid B-ring en route to estratrienes

Authors:	Pavel Herrmann

Institution:	Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic Institute of Organic Chemistry and Biochemistry, Flemingovo nám. 2, 166 10 Praha 6, Czech Republic

Abstract:	Zirconocene catalyzed cyclization of 2-(5-methoxy-3-penten-1-yl)styrene in the presence of organomagnesium reagents was studied. The cyclization proceeded in high isolated yields (up to 84%) with excellent trans-selectivity (>98%), which is unusual for the formation of cyclohexane derivatives. Catalytic cyclization in the presence of Cp₂ZrCl₂ proceeded as well with similar results. The reaction with (R,R)-(EBTHI)₂ZrCl₂ gave a cis/trans mixture of 5 in low yield and poor ee.

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