Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization

Demir A.

TETRAHEDRON, vol.57, no.1, pp.227-233, 2001 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 1
  • Publication Date: 2001
  • Doi Number: 10.1016/s0040-4020(00)01002-4
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.227-233
  • Keywords: epoxides, dienes, steroid and sterols, aromatization, CRETACEOUS BLACK SHALES, SECONDARY ALCOHOLS, DEHYDRATION, 5,6-EPOXIDES
  • Middle East Technical University Affiliated: Yes

Abstract

The reaction of tetramethyldiamidophosphoric acid chloride with epoxides in the presence of a trace amount of water furnished 1,3-dienes in good yield. The conversion works with open chain and cyclic epoxides. A C-C bond cleavage reaction occurs if the epoxide contains a quaternary carbon. Application of this method to epoxy sterols afforded ring A aromatic steroids in good yield. The aromatization works via dienol-benzene rearrangements and is independent of the C-3 stereochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.