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A mechanistic study on the Hooker oxidation: synthesis of novel indane carboxylic acid derivatives from lapachol.
MedLine Citation:
PMID:  23196897     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The Hooker oxidation is one of the most intriguing transformations wherein lapachol () is readily converted to norlapachol () in very good yield. This one-pot reaction involves a very intricate mechanism in which the alkyl side chain of lapachol is shortened by one carbon unit. Previous studies have unequivocally established the involvement of an indane carboxylic acid derivative , as a key intermediate (Hooker intermediate), and its simultaneous conversion to norlapachol () via the oxidative cleavage of vicinol diol and subsequent intramolecular aldol reaction of the resulting keto acid. However, the formation of the key Hooker intermediate from lapachol () remains ambiguous. The present study has thrown some light on the formation of the key intermediate from lapachol () via benzilic acid rearrangement of the corresponding labile o-diquinone intermediate derived from lapachol. The involvement of o-diquinone intermediate in the Hooker oxidation has been further established by trapping of this labile intermediate as the corresponding phenazine derivative . The involvement of benzilic acid rearrangement as a key step in the Hooker oxidation is further shown with a variety of o-quinones prepared from lapachol ().
Authors:
Kenneth O Eyong; Manohar Puppala; Ponminor Senthil Kumar; Marc Lamshöft; Gabriel N Folefoc; Michael Spiteller; Sundarababu Baskaran
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-30
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India. sbhaskar@iitm.ac.in.
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