Study towards bioactive pyrone derivatives from the marine red alga Phacelocarpus labillardieri

Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A 2 inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivor...

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Bibliographic Details
Published in:Tetrahedron 2003-08, Vol.59 (35), p.6899-6904
Main Authors: Song, Dschun, Blond, Gaëlle, Fürstner, Alois
Format: Article
Language:English
Subjects:
alkynes
macrocycles
marine natural products
metathesis
pyrone
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Summary:Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A 2 inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivorous gastropods. Described herein is the first preparative study towards these conspicuous secondary metabolites. Their carbon skeleton has been assembled in a few straightforward steps using ring closing alkyne metathesis (RCAM) catalyzed by the Schrock alkylidyne complex ( tBuO) 3WCCMe 3 to forge the meta-cyclophane core with high efficiency. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00815-9