Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis

Identification of amphilectosins as key ...

Title	Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis
Author(s)	T. Ferns, R. 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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