A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid (Articolo in rivista)

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  • A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2013.07.011 (literal)
Alternative label
  • Serra, Stefano; Cominetti, Alessandra A. (2013)
    A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Serra, Stefano; Cominetti, Alessandra A. (literal)
Pagina inizio
  • 1110 (literal)
Pagina fine
  • 1116 (literal)
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  • 24 (literal)
Rivista
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  • 7 (literal)
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  • 18 (literal)
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  • ISI Web of Science (WoS) (literal)
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  • CNR Ist Chim Riconoscimento Mol (literal)
Titolo
  • A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid (literal)
Abstract
  • The combined use of the Sharpless asymmetric epoxidation, a number of stereospecific chemical transformations, and the 3,5-hexadienoic acid benzannulation protocol allowed us to devise a new, divergent, and stereoselective approach to terpenes with a chiral tertiary hydroxyl group at the ortho-position of a phenol functional group. Accordingly, the natural occurring enantiomeric forms of the bisabolane sesquiterpenes (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid were synthesized with high enantiomeric purity starting from geraniol. The latter two acids were prepared in enantioenriched form for the first time. (C) 2013 Elsevier Ltd. All rights reserved. (literal)
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