Structure revision and assignment of absolute stereochemistry of a marine C21 bisfuranoterpene.
The C21 bisfuranoterpene (-)-isotetradehydrofurospongin-1 (6), previously isolated from a Western Australian Spongia sp., has been reisolated from a specimen of Spirastrella papilosa collected during scientific trawling operations in the Great Australian Bight. A 2D NMR analysis of 6 has prompted reassignment of the published structure 5, while degradation and chiral HPLC analysis have allowed determination of the absolute stereochemistry.
Capon
R J
RJ
School of Chemistry, University of Melbourne, Parkville, Victoria, 3010, Australia. r.capon@unimelb.edu.au
Jenkins
A
A
Rooney
F
F
Ghisalberti
E L
EL
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010126:Ozone; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; C433914:isotetradehydrofurospongin-1; D010126:Ozone