Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization

Demir A.

TETRAHEDRON, cilt.57, sa.1, ss.227-233, 2001 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 57 Sayı: 1
  • Basım Tarihi: 2001
  • Doi Numarası: 10.1016/s0040-4020(00)01002-4
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.227-233
  • Anahtar Kelimeler: epoxides, dienes, steroid and sterols, aromatization, CRETACEOUS BLACK SHALES, SECONDARY ALCOHOLS, DEHYDRATION, 5,6-EPOXIDES
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.