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Structure of the diene originating from a retro ‐Diels–Alder cleavage, of the natural product kuwanon g
Author(s) -
Takayama Mitsuo,
Nomura Taro,
Nojima Kazutetsu
Publication year - 1995
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290090505
Subject(s) - chemistry , diene , fragmentation (computing) , adduct , tautomer , moiety , dissociation (chemistry) , stereochemistry , cleavage (geology) , ion , photochemistry , medicinal chemistry , organic chemistry , natural rubber , geotechnical engineering , fracture (geology) , computer science , engineering , operating system
Abstract Fragmentation of a natural Diels–Alder adduct, kuwanon G, has been examined using fast‐atom bombardment and collision‐induced dissociation (CID) techniques. The CID spectrum of a diene ion originating from a retro ‐Diels–Alder cleavage of the [M + H] + ion gave an intense peak arising from the fragmentation of the diene moiety, as well as characteristic peaks arising from the fragmentation of a tautomeric 2,2‐dimethylpyran ring structure. The results obtained suggest that the diene can be irreversibly converted into the 2,2‐dimethylpyran ring structure under gas‐phase mass spectrometric conditions.