title: Plumeridoid C from the Amazonian traditional medicinal plant Himatanthus sucuuba.
abstract: The stereochemistry of the iridoid plumeridoid C, C(15)H(18)O(7), 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.
authors: Institute of Pharmacy, University of Innsbruck, Innrain 52c, 6020 Innsbruck, Austria.
authors: Birgit
authors: B
authors: Waltenberger
authors: Judith M
authors: JM
authors: Rollinger
authors: Ulrich J
authors: UJ
authors: Griesser
authors: Hermann
authors: H
authors: Stuppner
authors: Thomas
authors: T
authors: Gelbrich
mesh_terms: D029062:Apocynaceae / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C569585:(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; D005663:Furans; D011714:Pyrans; D013141:Spiro Compounds