Novel steroid mimics directed towards the estradiol skeleton

Bridgeman, Eve and Cavill, Julie L. and Schofield, Daniel J. and Wilkins, Derek S. and Tomkinson, Nicholas C. O. (2005) Novel steroid mimics directed towards the estradiol skeleton. Tetrahedron Letters, 46 (49). pp. 8521-8524. ISSN 0040-4039

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Abstract

A series of non-sym. tri- and tetra-substituted ureas, e.g. I (R = H, Me) were prepd. to mimic the rigid tetracyclic core of estradiol. Tetra-substituted ureas were prepd. by a five-step protocol, involving activation and displacement of a carbonyldiimidazole adduct in 48-67% overall yield. This method was unsuccessful for tri-substituted ureas, which were prepd. in 42-74% yields by an alternative four-step method, which included a one-pot 4-nitrophenyl carbamate formation/displacement sequence.