Plumeridoid C from the Amazonian traditional medicinal plant
The stereochemistry of the iridoid plumeridoid C, C15H18O7, was established by X‐ray single‐crystal structure analysis, giving (2′R,3R,4R,4aS,7aR)‐methyl 3‐hydroxy‐4′‐[(S)‐1‐hydroxyethyl]‐5′‐oxo‐3,4,4a,7a‐tetrahydro‐1H,5′H‐spiro[cyclopenta[c]pyran‐7,2′‐furan]‐4‐carboxylate. The absolute structure of the title compound was determined on the basis of the Flack x parameter and Bayesian statistics on Bijvoet differences. The hydrogen‐bond donor and acceptor functions of the two hydroxy groups are employed in the formation of O—H...O‐bonded helical chains.
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Document Type: Research Article
Affiliations: Institute of Pharmacy, University of Innsbruck, Innrain 52c, 6020 Innsbruck, Austria
Publication date: October 15, 2011