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Syntheses of (+)-.alpha.- and (+)-.beta.-eudesmol and their diastereomers by intramolecular nitrone-olefin cycloaddition

Published on May 1, 1985in Journal of Organic Chemistry 4.75
· DOI :10.1021/jo00209a003
Martin A. Schwartz91
Estimated H-index: 91
Ann M. Willbrand1
Estimated H-index: 1
  • References (0)
  • Citations (23)
Cited By23
Published on Sep 14, 2018in Biochemical Journal 4.33
Yuru Tong1
Estimated H-index: 1
(SPU: Shenyang Pharmaceutical University),
Ping Su2
Estimated H-index: 2
(National Resource Center)
+ 8 AuthorsLuqi Huang28
Estimated H-index: 28
(SPU: Shenyang Pharmaceutical University)
Cryptomeridiol, a typical eudesmane diol, is the active principle component of the antispasmodic Proximol. Although it has been used for many years, the biosynthesis pathway of cryptomeridiol has remained blur. Among terpenoid natural products, terpenoid cyclases are responsible for cyclization and generation of hydrocarbon backbones. The cyclization is mediated by carbocationic cascades and ultimately terminated via deprotonation or nucleophilic capture. Isoprene precursors are, respectively, c...
Published on Jul 2, 2016in Natural Product Research 2.00
Xiaoqing Hu2
Estimated H-index: 2
(MUC: Minzu University of China),
Xianjin Sui1
Estimated H-index: 1
(MUC: Minzu University of China)
+ 5 AuthorsFeng Zhang1
Estimated H-index: 1
(MUC: Minzu University of China)
AbstractThe comet assay-guided fractionation of the twigs of Manglietia hookeri resulted in the isolation of three sesquiterpene-neolignans, including a new one 5-allyl-2-(4-allyl-phenoxy)-3-[7-(1-hydroxy-1-methyl-ethyl)-1, 4a-dimethyl-decahydro-naphthalen-1-yloxy]-phenol (1), and eudesobovatol A (2) and eudesobovatol B (3), together with three lignans, obovatol (4), honokiol (5) and magnolol (6). Their structures were elucidated on the basis of spectral analysis and by comparison with related l...
Published on Nov 10, 2009in Natural Product Research 2.00
Berenice Aguilar-Guadarrama4
Estimated H-index: 4
(Universidad Autónoma del Estado de Morelos),
Víctor Navarro1
Estimated H-index: 1
(Universidad Autónoma del Estado de Morelos)
+ 1 AuthorsMaría Yolanda Rios17
Estimated H-index: 17
(Universidad Autónoma del Estado de Morelos)
Secondary metabolites 5-acetyl-3β-angeloyloxy-2β-(1-hydroxyisopropyl)-2,3-dihydrobenzofurane (1), 5-acetyl-3β-angeloyloxy-2β-(1-hydroxyisopropyl)-6-methoxy-2,3-dihydrobenzofurane (2), espeletone (3), encecalinol (4), O-methylencecalinol (5), encecalin (6), sonorol (7), taraxerol (8), (+)-β-eudesmol (9), and a mixture of β-sitosterol and stigmasterol, were isolated from the aerial parts of Ageratina pichinchensis var. bustamenta. The antimicrobial activity of compounds 6, 8 and 9, together with d...
Remo Gandolfig (UNIPV: University of Pavia), Paolo Grünanger8
Estimated H-index: 8
(UNIPV: University of Pavia)
Published on Sep 1, 2001in Tetrahedron 2.38
Gianluigi Broggini26
Estimated H-index: 26
C. La Rosa14
Estimated H-index: 14
(University of Milan)
+ 2 AuthorsGaetano Zecchi20
Estimated H-index: 20
Abstract Intramolecular cycloadditions of unsaturated nitrones derived from a series of N -(2-alkenyl)-2-pyrrolecarbaldehydes ( 2 ) have been systematically studied. A pronounced substituent effect has been observed as far as the competitive formation of fused- and bridged-ring regioisomers are concerned. Further elaboration of the two kinds of cycloadducts has given pyrrolizidine and indolizidine derivatives, respectively.
Published on Oct 1, 1999in Phytochemistry 2.90
Masao Toyota31
Estimated H-index: 31
(Tokushima Bunri University),
Yumiko Yonehara1
Estimated H-index: 1
(Tokushima Bunri University)
+ 2 AuthorsYoshinori Asakawa43
Estimated H-index: 43
(Tokushima Bunri University)
Abstract The ether extract of the liverwort Porella perrottetiana afforded (−)-α-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (−)-α-eudesmol strongly suggested that the positive values (e.g.+28.5°) described in many previous papers should be revised. Since the absolute configuration of (−)-α-eudesmol was identical to that of (+)-β-eudesmol found in the higher plants, it was appa...
Published on Mar 1, 1996in Journal of Essential Oil Research 1.23
Philip S. Beauchamp9
Estimated H-index: 9
(CPP: California State Polytechnic University, Pomona),
Vasu Dev11
Estimated H-index: 11
(CPP: California State Polytechnic University, Pomona)
+ 5 AuthorsAlbert T. Bottini14
Estimated H-index: 14
(UC Davis: University of California, Davis)
ABSTRACT The leaf oil of Cymbopogon distans (Steud.) Wats, chemotype Loharhket and the root oil of Cymbopogon jwarancusa (Jones) Schult. were examined by GC and GC/MS and found to qualitatively exhibit a very similar sesquiterpenoid composition. The sesquiterpenoid content of the C. Distans and C. Jwarancusa oils was 79.6% and 38.0%, respectively. Most of the sesquiterpenoids were isolated by liquid chromatography and their structures assigned on the basis of their IR, MS, 1H- and 13C-NMR spectr...
Published in Tetrahedron 2.38
Albert Padwa6
Estimated H-index: 6
(Emory University),
Steven J. Coats14
Estimated H-index: 14
(Emory University),
Mark A. Semones13
Estimated H-index: 13
(Emory University)
Abstract A series of 3,3-disubstituted bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides are easily prepared from the reaction of 3H-thiolactams with 1,3-bielectrophiles. These cross-conjugated heteroaromatic betaines undergo regio- and diastereospecific 1,4-dipolar cycloaddition with electron-rich and electron-deficient π-bonds to produce 1,4-cycloadducts containing a carbonyl sulfide bridge. A representative betaine dipole and a 1,4-cycloadduct were characterized by single crystal X-r...
Published on Dec 1, 1992in Phytochemistry 2.90
Hans Achenbach26
Estimated H-index: 26
(FAU: University of Erlangen-Nuremberg),
Dieter Frey2
Estimated H-index: 2
(FAU: University of Erlangen-Nuremberg)
Abstract From the petrol extract of the stem bark of Monocyclanthus vignei 30 terpenoids and two phenylpropanoids have been isolated and their structures established, among them 17 new cycloartane-type compounds. Geranic acid and β-caryophyllene were found to be the major constituents.