Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/101494
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Type: Journal article
Title: Some chemical speculation on the biosynthesis of corallidictyals A-D
Author: Markwell-Heys, A.
George, J.
Citation: Organic and Biomolecular Chemistry, 2016; 14(24):5546-5549
Publisher: Royal Society of Chemistry
Issue Date: 2016
ISSN: 1477-0520
1477-0539
Statement of
Responsibility: 
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
RMID: 0030044917
DOI: 10.1039/c6ob00171h
Grant ID: http://purl.org/au-research/grants/arc/DP160103393
Appears in Collections:Chemistry publications

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