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American Chemical Society, Journal of Natural Products, 11(75), p. 1944-1950, 2012

DOI: 10.1021/np300518j

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Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer

Journal article published in 2012 by Francesca Leonelli, Valentina Latini, Andrea Trombetta, Gabriele Bartoli, Francesca Ceccacci ORCID, Angela La Bella, Alessio Sferrazza, Doriano Lamba ORCID, Luisa Maria Migneco, Rinaldo Marini Bettolo
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

(+)-2-Deoxyoryzalexin S (1), the nominal enantiomer of a diterpenoid isolated in Chile from Calceolaria species, was regio- and diastereoselectively synthesized from (+)-podocarpic acid. (+)-2-Deoxyoryzalexin S (1) was characterized also as its acetyl derivative, (+)-2, whose structure was confirmed by X-ray crystallographic analysis. Surprisingly, comparison of the data recorded for (+)-1 and (+)-2 and those reported in the literature for the Calceolaria isolated diterpenoid 1 and its derivative (-)-2 showed some differences, suggesting that the latter do not possess the proposed structures.