Identification of amphilectosins as key ...



Title Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis
Author(s) T. A. Ferns, Russell G. Kerr
Journal The Journal of Organic Chemistry
Date 2005
Volume 70
Issue 16
Start page 6152
End page 6157
Abstract Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites provide the biosynthetic link between the seco-pseudopterosins (serrulatane diterpenes) and pseudopterosins (amphilectane diterpenes). This biosynthetic relationship was confirmed through various radiolabeling experiments. Incubation studies with the amphilectosins revealed the selective transformation of amphilectosin A to pseudopterosin Y and the transformation of amphilectosin B to pseudopterosin F, which suggests that the alpha/beta stereochemistry for the isobutenyl group in the pseudopterosins arises from the selective ring closure of the cis- and trans-amphilectosins.
DOI 10.1021/jo050282r
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