Sylvone, a new furanoid lignan of Piper sylvaticum
TL;DR: The structure of a 2,3,4 trisubstituted furanoid lignan, designated sylvone, was established as 1 from detailed spectroscopical and chemical studies as discussed by the authors.
About: This article is published in Tetrahedron.The article was published on 1984-01-01. It has received 19 citations till now.
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TL;DR: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed in this paper, where nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references.
849 citations
TL;DR: The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products.
Abstract: The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products. The reactions proceed with complete 3,4-trans stereoselectivity, whereas the C-2 stereochemistry depends on both the aldehyde and Lewis acid used. When boron trifluoride etherate is used with aliphatic or electronically neutral aryl aldehydes, the reactions favor the production of the 2,3-cis isomer 8, whereas electron-rich aryl aldehydes lead to the 2,3-trans isomer 9 by Lewis acid-mediated isomerization of the kinetically favored cis isomer. The isomerization can be avoided by use of TMSOTf as a promoter, and hence, the stereochemistry can be tuned by appropriate choice of reagent. Cleavage of the pendant 3-ethenyl group installs the 3-hydroxymethyl group common to the furanolignans.
67 citations
TL;DR: The structures and conformations of three new lignans, wikstrone (1), wikstroemol (2), and wikstemone (3), isolated from the aerial parts of Wikstroemia hainanensis, were determined, together with those of twelve known compounds, including erythro-guaiacylglycerol-β-O-4′-sinapyl ether (4).
Abstract: The structures and conformations of three new lignans, wikstrone (1), wikstroemol (2), and wikstroemone (3) – isolated from the aerial parts of Wikstroemia hainanensis – were determined, together with those of twelve known compounds, including erythro-guaiacylglycerol-β-O-4′-sinapyl ether (4). The configuration of 4, falsely assigned in the literature (threo configuration), was redetermined, and the compound was identified as erythro-guaiacylglycerol-β-O-4′-sinapyl ether.
48 citations
TL;DR: A new tetrahydrofuranoid lignan, altissinone and a new acylated flavone C-glucoside, 2''-O-p-hydroxybenzoylorientin were isolated in addition to several known triterpene acids and flavonoids from the ethyl acetate extractives of the leaves of Vitex altissima.
45 citations
TL;DR: From the twigs of Taxus mairei, 35 lignans, 2 sesquilignans and 4 flavonoids, 3 bisflavonoid, 13 phenolic derivatives, 2 bisnorsesquiterpenes, 3 long-chain carboxylic acids and 4 steroids were isolated as mentioned in this paper.
Abstract: From the twigs of Taxus mairei, 35 lignans, 2 sesquilignans, 4 flavonoids, 3 bisflavonoids, 13 phenolic derivatives, 2 sesquiterpenes, 3 bisnorsesquiterpenes, 3 long-chain carboxylic acids and 4 steroids were isolated. The new lignans and phenolic glucosides include 7′-hydroxynortrachelogenin, 7-hydroxymatairesinol, 3′-O-demethylepipinoresinol, taxiresinol 9-acetate, 3′-O-demethyltanegool, 8′-epitanegool, 3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one, 3-O-demethyldihydrodehydrodiconiferyl alcohol, taxumaiglucoside A heptaacetate, taxumaiglucoside B heptaacetate, and taxumaiglucoside C heptaacetate. Their structures were determined by spectral methods.
38 citations
References
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TL;DR: Four lignans were isolated from the flower buds of Magnolia fargesii Cheng, two of which were known lignan, pinoresinol dimethyl ether and liriores inol-B dim methyl ether; the other two were new lignANS, magnolin and fargein.
53 citations
TL;DR: The structure of sylvatine (1), a new alkamide from Piper sylvaticum, has been elucidated from spectroscopic studies, chemical reactions and correlation with compounds of known structures as mentioned in this paper.
15 citations
TL;DR: Sylvamide, a new amide derivative, has been isolated from the petrol extract of the seeds of Piper sylvaticum (Roxb) from spectral and chemical properties as discussed by the authors.
10 citations
TL;DR: Spektroskopische Strukturaufklärung eines Inhaltsstoffes (Alkaloid) aus Piper sylvaticum Roxb.
Abstract: Spektroskopische Strukturaufklarung eines Inhaltsstoffes (Alkaloid) ausPiper sylvaticum Roxb. mit teils synthetischer Beweisfuhrung.
7 citations