Novel steroid mimics directed towards the estradiol skeleton

Eve Bridgeman, Julie L. Cavill, Daniel J. Schofield, Derek S. Wilkins, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

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.
Original languageUndefined/Unknown
Pages (from-to)8521-8524
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number49
DOIs
Publication statusPublished - 2005

Keywords

  • estradiol skeleton
  • steroid
  • carbonyldiimidazole adduct
  • tetra-substituted ureas

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