Circular dichroism and conformations of pterosins, 1-indanone derivatives from bracken.

Kuroyanagi, Masanori; Fukuoka, Masamichi; Yoshihira, Kunitoshi; Natori, Shinsaku

doi:10.1248/cpb.27.731

Cited by 32 publications

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“…For "C nrnr spectra, peak positions were assigned relative to the CHCI, resonances at 78. 16 Column chromatography was carried out with silica gel (230-400 mesh) and thin layer chromatography with silica gel 60 F-245 plates (E. Merck Laboratories).…”

Section: Methodsmentioning

confidence: 99%

“…All four pterosin C isomers have been isolated from bracken, the 2R,3R isomer and 2S,3R isomer (as its glucoside at the primary hydroxyl) from rhizomes, and the 2R,3S and 2S,3S isomers from fronds (15). The cis and trans isomers can be readily distinguished by their nmr spectra.…”

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confidence: 99%

“…The cd (circular dichroism) curves of mixtures of cis and trans isomers exhibited nearly the same ellipticity values irrespective of the ratio of cis to trans (16). A mixture with ratio of 2R,3S:2S,3S = 1 : 2 had [0]3?6 +20 688 and for the ratio 1 :4, ['0]>26 +22 939.…”

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confidence: 99%

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An efficient synthesis of pterosin C and other pterosins

Ng¹,

McMorris²

1984

Can. J. Chem.

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A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

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Section: Methodsmentioning

confidence: 99%

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An efficient synthesis of pterosin C and other pterosins

Ng¹,

McMorris²

1984

Can. J. Chem.

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“…This compound, mp 160-162"C, has a molecular formula C14Hl,03 and was identified as (2R,3R)-pterosin C (13), a known norsesquiterpene isolated from Pteridium ferns, by comparison of spectroscopic (ir, 'H nmr) and physical (mp, rotation) data with published values (12-14). Roughly two dozen 1-indanone sesquiterpenoids and norsesquiterpenoids with the skeleton of 13 and collectively known as the pterosins have been isolated from ferns (14,15). The pterosins belong to the so-called illudalane class of sesquiterpenes, compounds which have the carbon skeleton 14 (16).…”

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confidence: 99%

“…The illudalanes are in turn secoilludanes, the illudanes possessing the carbon skeleton 15 (16). It is tempting to speculate that the biosynthesis of the cybrodins proceeds from farnesyl pyrophosphate via humulene, a protoilludane, an illudane, and an illudalane (14) intermediate. 'j Pterosin L (16), or a derivative thereof, by retroaldolization involving the C-3 hydroxyl (indanone numbering) and the C-1 carbonyl (or a suitable leaving group) could give rise to the cybrodin skeleton.…”

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The cybrodins, a new class of sesquiterpenes

Ayer¹,

McCaskill²

1981

Can. J. Chem.

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. Can. J. Chem. 59, 2150Chem. 59, (1981. The isolation and structure determination of the "cybrodins", a new group of sesquiterpenoids produced by a new strain of the bird's nest fungus Cyathus bulleri, is reported. Cybrodol(3), isocybrodol(4), cybrodal (5), trisnorcybrodolide (6), and cybrodic acid (7) may be classified as seco-illudalane sesquiterpenes. The evidence leading to the structural assignments is presented, along with chemical correlations among the cybrodins. The possible mode of biogenesis is discussed. Pterosin-C (13), a known norsesquiterpene, and 3-methyllumichrome (17) were also isolated. Small quantities of a new sesquiterpenoid, broderol, believed to possess structure 21, were obtained on two occasions. WILLIAM A. AYER and ROBERT H. MCCASKILL. Can. J. Chem. 59,2150Chem. 59, (1981. On rapporte la separation et la determination de la structure des "cybrodines", un nouveau groupe de sesquiterpenes produits par une nouvelle deformation du champignon des nidsd'oiseaux: le Cyarhus bulleri. On peut classifier le cybrodole (3), I'isocybrodole (4), le cybrodale (S), le trisnorcybrodolide (6) et I'acide cybrodique (7) comme des sesquiterpenes du type seco-illudalane. On prtsente des donnees qui permettent d'attribuer des structures ainsi que les correlations chimiques entre les cybrodines. On discute du mode possible de biogenkse. On a egalement isole la pterosine-C (13) un norsesquiterpenes connu ainsi que la methyl-3 lumichrome (17). On a obtenu a deux reprises des petites quantites de broderol, un nouveau sesquiterpene qui posskderait la structure 21.[Traduit par le journal]Some time ago we reported the isolation and we describe the total syntheses of the cybrodins. The ethyl acetate soluble metabolites were divided 'Stock cultures of the strain used previously no longer produced 1 or the triol.into neutral and acidic components by extraction 4The compounds are named in honor of Harold J. Brodie, with aqueous sodium bicarbonate. The metabolites Professor Emeritus, University of Alberta, the discoverer of were further separated by chromatography over this species of Cyathus. Sephadex LH-20 (this separates the metabolites

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Chiroptical Properties of Compounds ContainingCOGroups

Boiadjiev

Lightner

2009

Patai's Chemistry of Functional Groups

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Introduction The Octant Rule Compilation of Ketone and Aldehyde CD Unsaturated Ketones Compilation of Unsaturated Ketone and Aldehyde CD Exciton Chirality Addendum Acknowledgments

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Circular dichroism and conformations of pterosins, 1-indanone derivatives from bracken.

Cited by 32 publications

References 0 publications

An efficient synthesis of pterosin C and other pterosins

An efficient synthesis of pterosin C and other pterosins

The cybrodins, a new class of sesquiterpenes

Chiroptical Properties of Compounds ContainingCOGroups

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