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The biomimetic synthesis of trans-(1β-h,5α-h)-guaianolides

AuthorsGonzález, Antonio G.; Galindo, Antonio ; Afonso, M. Mar; Mansilla, Horacio ; Palenzuela, José A.; Gómez Rodríguez, Mª Ángeles; Martínez-Ripoll, Martín
Issue Date1988
CitationTetrahedron 44(14): 4575-4584 (1988)
Abstract1-epigallicin 11 underwent biomimetic cyclization to trans-(1β-H,5α-H)-guaianolide 22,the stereoespecificity of this cyclization being credited to the fact that it took place via the reacting TC conformation 27. The epimeric nor-guaianolides 15 and 17 were prepared and their rearrangements studied. The biogenetic implications of these processes are discussed.
Description10 pages, 4 figures, 5 tables, 2 schemes.
Lists of observed and calculated structure factors, final anisotrooic parameters for heavy atoms, positional and thermal parameters for H-atoms, are available from the Cambridge Crystallographic Data Centre (CCDC), University Chemical Laboratory, Lensfield Road, Cambridge CB2.
Publisher version (URL)http://dx.doi.org/10.1016/S0040-4020(01)86160-3
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