Abstract
An efficient synthesis of ent-halimanolide 2 (15,16-epoxy-12-oxo-ent-halima-5(10),13(16),14-trien-18,2β-olide), from ent-halimic acid has been achieved, corroborating the structure of the natural compound and establishing its absolute configuration.
Highlights
Euphorbiaceae plants are a rich source of bioactive substances [1,2] and certain genera of this family have attracted much interest, since they contain a group of antitumor compounds [3].Cladogynos orientalis Zipp. ex Span
We report the synthesis of ent-halimanolide 2, in order to confirm the structure of the natural compound and do SAR studies. ent-Halimanolide is a furan diterpene like chettaphanin I
Two synthetic routes have been explored for the synthesis of 2: Route A and Route B, which differ in the strategy followed for the preparation of the γ-lactone, before or after of the introduction of the furan ring
Summary
Euphorbiaceae plants are a rich source of bioactive substances [1,2] and certain genera of this family have attracted much interest, since they contain a group of antitumor compounds [3]. Chettaphanin I [4,5] and II [6,7], are the main components from their roots of this plant and the first to be known. In addition to chettaphanin I and II, Molecules 2008, 13 isolation from the root extract of a series of furan diterpenes 2-4 with ent-halimane skeletons has been described [8]. Structures of furo-ent-halimanes from Cladogynos orientalis and ent-halimic acid. Our group has transformed ent-halimic acid 1, a diterpene of known structure and absolute configuration, into chettaphanin I and II, which confirmed their structure and absolute configuration [4, 6]. Ent-Halimanolide is a furan diterpene like chettaphanin I and II, but in this case the carboxylic acid at C-18 has formed a γ-butanolide with the hydroxyl at C-2 We report the synthesis of ent-halimanolide 2, in order to confirm the structure of the natural compound and do SAR studies. ent-Halimanolide is a furan diterpene like chettaphanin I and II, but in this case the carboxylic acid at C-18 has formed a γ-butanolide with the hydroxyl at C-2
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