title: Some chemical speculation on the biosynthesis of corallidictyals A-D.
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.
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia. jonathan.george@adelaide.edu.au.
authors.forename: Adrian W
authors.initials: AW
authors.lastname: Markwell-Heys
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: George
mesh_terms: D000818:Animals; D003500:Cyclization; D010084:Oxidation-Reduction; D011161:Porifera / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D012717:Sesquiterpenes; C586604:corallidictyal D; C091979:corallidictyal A