Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization
TETRAHEDRON, vol.57, no.1, pp.227-233, 2001 (SCI-Expanded, Scopus)
- 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.