Synthesis of 7a-Substituted Hajos−Wiechert Ketone Analogues

A general and efficient route to 2-substituted 1,3-cyclopentadiones 3 has been developed. This operationally simple, two-step procedure is amenable to multigram scale preparations of these useful synthetic intermediates. These compounds are then transformed to previously unknown, higher analogues of...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 73; no. 13; pp. 5151 - 5154
Main Authors Kennedy, Jason W. J, Vietrich, Sophia, Weinmann, Hilmar, Brittain, Dominic E. A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.07.2008
Amer Chemical Soc
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
CATALYSIS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
STEROIDS
MICHAEL
CONSTRUCTION
Enantioselectivity
Knoevenagel condensation
Analog
Aromatic compound
Indene derivatives
Robinson annelation
Chemical synthesis
Ketone
Enone
Hydrogenation
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Summary:A general and efficient route to 2-substituted 1,3-cyclopentadiones 3 has been developed. This operationally simple, two-step procedure is amenable to multigram scale preparations of these useful synthetic intermediates. These compounds are then transformed to previously unknown, higher analogues of the Hajos−Parrish−Eder−Sauer−Wiechert ketone (enone 1, R = Me) following an enantioselective Robinson annulation.
Bibliography:ark:/67375/TPS-DSGCT4W2-F
istex:2C8E76357D839965928826FEEF8E267AEDE564BA
Complete experimental and characterization data for all compounds reported in this paper, details of the optimization studies for the aldol cyclization and the large scale preparation of enone 1c, and X-ray crystal structure data for enone 1c. This material is available free of charge via the Internet at http://pubs.acs.org.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800638s