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A novel rearrangement in the acid-catalyzed O-demethylation of a 6,14-endo-ethenotetrahydrothebaine using hydrobromic acid

✍ Scribed by Yibin Zeng; Jie Yang; Zhuibai Qiu; Jian Cheng; Chunhua Hu; Peiju Zhen

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 132 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02283-3

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✦ Synopsis

A new rearrangement byproduct, 3-methyl-1,2,3,4,4a,4b,9a,15,15a,15b-decahydro-(4,5);(4a,15)-dimethanotricyclo-(4,3,1,0 2,7 )deca[8,9,1,10-a,b,c]pyrido[4,3-a]-acridin-6-en-9-ol-8-one, has been isolated from the acid-catalyzed O-demethylation of 7a-o-aminophenyl-6,14-endo-ethenotetrahydrothebaine. The mechanism of its formation involving a novel annulation of the 6,14-endo-ethenylene moiety with the A ring aromatic carbons is discussed.

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