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

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 co...

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Bibliographic Details
Published inChemistry : a European journal Vol. 10; no. 23; pp. 6015 - 6028
Main Authors Bose, Gopal, Ullah, Ehsan, Langer, Peter
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.12.2004
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cyclization
domino reactions
Physical Sciences
rearrangement
Science & Technology
silyl enol ethers
spiro compounds
BIOMIMETIC SYNTHESIS
ORGANIC-SYNTHESIS
MECHANISM
PYRROLOMYCIN-B
DIALKYLATION
cyclization
spiro compounds
ENOL SILYL ETHERS
domino reactions
BIOSYNTHESIS
CHEMISTRY
silyl enol ethers
DERIVATIVES
PARTICIPATION
rearrangments
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Summary: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. Die [3+3] Cyclisierung von 1,3‐Bis‐Silylenolethern mit 1,1‐Diacylcyclopentanen ermöglicht eine effiziente Synthese von Spiro[5.4]decenonen. Durch Behandlung dieser Verbindungen mit Trifluoressigsäure (TFA) konnte eine große Bandbreite von Bicyclo[4.4.0]deca‐1,4‐dien‐3‐onen mit angularer Alkylgruppe hergestellt werden. Dieses Gerüstsystem tritt in einer Reihe pharmakologisch relevanter Naturstoffe auf. Meeting in the middle: 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 variety of bicyclo[4.4.0]deca‐1,4‐dien‐3‐ones by domino “elimination–double‐Wagner–Meerwein‐rearrangement” reactions (see scheme; MS=molecular sieves).
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ark:/67375/WNG-WCDLT2CM-9
ArticleID:CHEM200400707
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200400707