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|Title:||Some chemical speculation on the biosynthesis of corallidictyals A-D|
|Citation:||Organic and Biomolecular Chemistry, 2016; 14(24):5546-5549|
|Publisher:||Royal Society of Chemistry|
|Adrian W. Markwell-Heys and Jonathan H. George|
|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.|
|Keywords:||Animals; Porifera; Sesquiterpenes; Cyclization; Oxidation-Reduction|
|Rights:||This journal is © The Royal Society of Chemistry 2016|
|Appears in Collections:||Chemistry publications|
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