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Some chemical speculation on the biosynthesis of corallidictyals A-D
Adrian W Markwell-Heys1, Jonathan H George
1Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia. jonathan.george@adelaide.edu.au.
Abstract:
The efficient conversion of siphonodictyal B into the spirocyclic natural products corallidictyals A-D has been achieved via oxidative and acid catalyzed cyclizations. The oxidative cyclization of siphonodictyal B occured spontaneously under aerobic oxidation conditions, which suggests that corallidictyals A and B are possibly artefacts of the isolation process. The mechanism of the oxidative cyclization of siphonodictyal B could be described as either an anionic 5-endo-trig cyclization (which is formally disfavoured by Baldwin's rules), or as an electrocyclic reaction, of an ortho-quinone intermediate.
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