Document Detail


Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B.
MedLine Citation:
PMID:  22531888     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The synthesis of the tricyclic angular chromone structure originally assigned to aspergillitine is reported. The synthesis was achieved in 11 steps and 15% overall yield from 2,4-dihydroxypropiophenone, through the intermediacy of 2,3-dimethyl-7-hydroxychromen-4-one. Construction of the nitrogen-bearing heterocyclic ring entailed a Stille cross-coupling reaction with n-Bu(3)SnCH(2)CH[double bond, length as m-dash]CH(2), followed by double bond isomerization, oximation of the chromone carbonyl, and a final microwave-assisted electrocyclization of the thus formed 6π-electron aza-triene system.
Authors:
Sebastián O Simonetti; Enrique L Larghi; Andrea B J Bracca; Teodoro S Kaufman
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-4-25
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  -     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-4-25     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:
Institute of Chemistry of Rosario (IQUIR, CONICET-UNR) and School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, S2002LRK Rosario, Argentina. kaufman@iquir-conicet.gov.ar.
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