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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 10
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Original Articles

Simple Synthesis of Deuterated Pterosines

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Pages 1553-1559 | Received 06 Sep 2007, Published online: 24 Apr 2008

References

  • Niwa , H. , Ojika , M. , Wakamatsu , K. , Yamada , K. , Hirono , I. and Matsushita , K. 1983 . Ptaquiloside, a potent carcinogen isolated from bracken fern Pteridium Aquilinum var. latiusculum: Structure elucidation based on chemical and spectral evidence, and reactions with amino acids, nucleosides, and nucleotides . Tetrahedron Lett. , 24 : 4117 – 4120 .
  • Ojika , M. , Wakamatsu , K. , Niwa , H. and Yamada , K. 1987 . Tetrahedron , 43 ( 22 ) : 5274
  • Castillo , U. F. , Wilkins , A. L. , Lauren , D. R. , Smith , B. L. and Alonso‐Amelot , M. 2003 . A new illudane‐type sesquiterpene glucoside from pteridium caudatum L. maxom, and the spectrometric characterization of caudatodienone . J. Agric. Food Chem. , 5 : 2559 and references therein
  • Evans , I. A. and Mason , J. 1965 . Carcinogenic activity of bracken . Nature , 208 : 913z
  • Hirono , I. and Yamada , K. 1990 . “ Bracken fern ” . In Naturally Occurring Carcinogens of Plant Origin 87 – 120 . Tokio and Amsterdam : Elsevier .
  • Borzacchiello , G. , Iovara , G. , Marcante , M. L. , Poggiali , F. , Roperto , F. and Venuti , A. 2003 . Presence of bovine papillomavirus type 2 DNA and expression of the viral oncoprotein e5 in naturally occurring urinary bladder tumours in cows . J. Gen. Virology , 84 : 2921
  • Kushida , T. , Usuegi , M. , Sugiura , M. , Kigoshi , H. , Tanaka , H. , Hirokawa , J. and Ojika , M. 1994 . DNA damage by ptaquiloside, a potent bracken carcinogen: Detection of selective strand breaks and identification of DNA cleavage products . J. Am. Chem. Soc. , 116 : 479
  • Alonso‐Amelot , M. E. 1997 . The link between bracken‐fern and stomach cancer: Milk . Nutrition , 13 ( 7–8 ) : 694 See inter alia
  • Saito , K. , Nagao , T. , Matoba , M. , Koyama , K. , Natori , S. , Marukami , T. and Saiki , Y. 1989 . Chemical assay of ptaquiloside, the carcinogen of pteridium aquilinum, and the distribution of related compounds in the pteridaceae . Phytochemistry , 28 ( 6 ) : 1605
  • Rasmussen , L. H. , Kroghsbo , S. , Frisvad , J. C. and Hansen , H. C. B. 2003 . Occurrence of the carcinogenic bracken constituent ptaquiloside in fronds, topsoil and organic soil layers in denmark . Chemosphere , 51 : 117 and references therein
  • Bonadies , F. , Borzacchiello , G. , Dezzi , S. , Nicoletti , R. and Roperto , S. 2004 . Mass spectrometric analysis of ptaquiloside, the toxic sesquiterpene from bracken fern . Rapid Comm. Mass Spectrom. , 18 : 825
  • Ayer , W. and McCaskill , R. 1981 . Metabolites of bird's nest fungi: The cybrodins, a new class of sesquiterpenes . Can. Journ. Chem. , 59 : 2150
  • Padwa , A. , Curtis , E. and Sandanayaka , V. 1996 . Generation and cycloaddition behavior of spirocyclic carbonyl ylides: Applicatio to the synthesis of the pterosin family of sesquiterpenes . J. Org. Chem. , 61 : 73 and references therein
  • Finkielsztein , L. M. , Alesso , E. , Lantano , B. , Aguirre , J. and Moltrasio Iglesias , G. 1999 . A simple synthetic route to pterosin f and other pterosines . J. Chem. Res, Minipr. , : 1561 – 1566 .

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