(+)-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.
Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer / Leonelli, Francesca; Valentina, Latini; Trombetta, Andrea; Gabriele, Bartoli; Francesca, Ceccacci; LA BELLA, Angela; Sferrazza, Alessio; Doriano, Lamba; Migneco, Luisa Maria; MARINI BETTOLO, Rinaldo. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 75:11(2012), pp. 1944-1950. [10.1021/np300518j]
Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer
LEONELLI, Francesca;TROMBETTA, ANDREA;LA BELLA, ANGELA;SFERRAZZA, ALESSIO;MIGNECO, Luisa Maria;MARINI BETTOLO, Rinaldo
2012
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.