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Synthesis of Spiro[5.4]decenones and Their Transformation into Bicyclo[4.4]deca‐1,4‐dien‐3‐ones by Domino “Elimination– Double‐Wagner–Meerwein‐Rearrangement” Reactions
Author(s) -
Bose Gopal,
Ullah Ehsan,
Langer Peter
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400707
Subject(s) - bicyclic molecule , trifluoroacetic acid , domino , chemistry , deca , alkyl , enol , stereochemistry , silylation , medicinal chemistry , organic chemistry , catalysis
The [3+3] cyclization of 1,3‐bis‐silyl enol ethers with 1,1‐diacylcyclopentanes allows a convenient synthesis of spiro[5.4]decenones. Treatment of these compounds with trifluoroacetic acid (TFA) afforded a great variety of bicyclo[4.4.0]deca‐1,4‐dien‐3‐ones containing an angular alkyl group. This core structure occurs in a number of pharmacologically relevant natural products.