Chemical and Pharmaceutical Bulletin
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Eight New Diterpenoids and Two New Nor-Diterpenoids from the Stems of Croton cascarilloides
Susumu KawakamiHiroki ToyodaLiva HarinantenainaKatsuyoshi MatsunamiHideaki OtsukaTakakazu ShinzatoYoshio TakedaMasatoshi KawahataKentaro Yamaguchi
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2013 Volume 61 Issue 4 Pages 411-418

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Abstract

From the stems of Croton cascarilloides, eight new diterpenoids, named crotocascarins A–H (1–8), having a crotofolane skeleton were isolated along with two new nor-diterpenoids (9 and 10), named crotocascarins α and β, derived through rearrangement of the crotofolane skeleton. The structures of these compounds were elucidated by means of extensive one- and two-dimensional NMR spectroscopic analyses. The absolute structures of the diterpene moiety were determined by application of the circular dichroism (CD) rule for the γ-lactone ring. The relative structures of the two crotofolanes (1 and 2) and one rearranged compound (9) were confirmed by X-ray crystallographic analyses. Compounds 1, 2 and 9 possessed 2-methylbutyric acid in their molecules, the absolute configuration of which was found to be 2S by comparison of its HPLC behavior with that of an authentic sample. Therefore, the absolute structures of these crotocascarins (1, 2 and 9) were unambiguously determined. The absolute structures of crotofolanes are reported for the first time in this paper.

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© 2013 The Pharmaceutical Society of Japan
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