Mass spectra of cyclopenin and viridicatin

Mass spectra of cyclopenin (I), viridicatin (III), 3-benzylidene-3,4-dihydro-4-methyl-1H-1,4-benzodiazepin-2,5-dione (VI) and derivatives of these systems were measured. Fragmentation schemes are proposed based on high resolution data, metastable peaks and, where appropriate, on deuterium labeling. The decomposition of I is found to follow pathways different in several respects from those proposed by Luckner et al. on the basis of low resolution spectra.

[1]  J. D. White,et al.  Stereospecific synthesis of dl-cyclopenin and dl-cyclopenol. , 1970, Tetrahedron.

[2]  H. Rapoport,et al.  Mechanism of the transformation of cyclopenin to viridicatin , 1969 .

[3]  H. Rapoport,et al.  Synthesis of cyclopenin and isocyclopenin , 1969 .

[4]  I. Lauder,et al.  The mass spectra of the furoquinol-4-one alkaloid acrophylline and quinol-2-ones related to hexahydroacrophylline , 1969 .

[5]  L. Nover,et al.  Thermische spaltung und massenspektrometrie der benzodiazepinalkaloide (−)-cyclopenin und (−)-cyclopenol , 1969 .

[6]  M. Luckner,et al.  [On the formation of quinoline alkaloids in plants. 4. Concerning the mechanism of cyclopenase activity]. , 1969, European journal of biochemistry.

[7]  J. Ballantine,et al.  Fragmentations in the mass spectra of 2‐oxo‐3‐indolyl derivatives , 1968 .

[8]  Dudley H. Williams,et al.  The mass spectra of some alkyl and aryl oxazoles , 1968 .

[9]  J. Reisch,et al.  Zur Bildung von Chinolinalkaloiden in Pflanzen , 1967 .

[10]  M. Luckner [On the synthesis of quinoline alkaloids in plants. 2. Fermentativ conversion of the penicillin alkaloids cyclopenin and cyclopenol to viridicatin and viridicatol]. , 1967, European journal of biochemistry.

[11]  R. Cooks,et al.  The mass spectra of acridones , 1967 .

[12]  L. Ehrenberg,et al.  Mass Spectrometry of Some Carbostyrils. , 1967 .

[13]  B. W. Erickson,et al.  Synthesis of 1-Deuterioaldehydes. Benzaldehyde-1-d , 1966 .

[14]  D. Maclean,et al.  MASS SPECTRA OF OXYGENATED QUINOLINES , 1966 .

[15]  Carabateas Pm,et al.  Analgesic antagonists. I. 4-substituted 1-acyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepines. , 1966 .

[16]  J. Shannon,et al.  Alkaloids of the Australian Rutaceae: Halfordia scleroxyla. III. Mass spectrometry of halfordinol and related oxazoles , 1965 .

[17]  C. E. Stickings,et al.  STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS. 114. VIRIDICATOL AND CYCLOPENOL, METABOLITES OF PENICILLIUM VIRIDICATUM WESTLING AND PENICILLIUM CYCLOPIUM WESTLING. , 1963, The Biochemical journal.

[18]  F. McLafferty 7 – Decompositions and Rearrangements of Organic Ions , 1963 .

[19]  B. Eistert,et al.  Notizen: Eine einfache Synthese des Viridicatins , 1962 .

[20]  A. Bracken,et al.  Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium Westling. , 1954, The Biochemical journal.