Isoeichlerianic acid from Aglaia silvestris and revision of the stereochemistry of foveolin B

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• 作者：Christoph Seger ; Silvia Pointinger ; Harald Greger ; Otmar Hofer
• 关键词：Dammarane triterpenes ; Shoreic acid ; Eichlerianic acid ; Isoeichlerianic acid ; Foveolins A and B
• 刊名：Tetrahedron Letters
• 出版年：2008
• 出版时间：30 June 2008
• 年：2008
• 卷：49
• 期：27
• 页码：4313-4315
• 全文大小：156 K

文摘

A new series of 20,24-epoxy (tetrahydrofuryl) type dammarane triterpenoids were established. So far two series were described, based on the stereochemistries of the tetrahydrofurane ring linked to the D ring of the triterpenoid skeleton. Eichlerianic acid was characterised by the absolute configuration (20S,24S) and shoreic acid by (20S,24R). Foveolins A and B were correlated with these compounds and published also as (20S,24S) and (20S,24R), respectively. ¹³C NMR analysis of a further stereoisomer of the acids isolated from Aglaia silvestris allowed the conclusion that the new isoeichlerianic acid, its methyl ester and the known foveolin B belonged to the new stereochemical series (20R,24S).