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Ciereszkolide: Isolation and Structure Characterization of a Novel Rearranged Cembrane from the Caribbean Sea Plume Pseudopterogorgia kallos
Author(s) -
Marrero Jeffrey,
Rodríguez Abimael D.,
Baran Peter,
Raptis Raphael G.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400292
Subject(s) - chemistry , carbon skeleton , olefin fiber , stereochemistry , chloroform , plume , crystallography , organic chemistry , catalysis , physics , thermodynamics
An investigation of the chloroform extract of a Colombian specimen of Pseudopterogorgia kallos has led to the isolation of a novel rearranged cembrane, ciereszkolide ( 1 ). The structure of 1 is based on a new carbon skeleton that possesses several unusual structural features, namely, two butyrolactones [one 2(3 H )‐ and one 2(5 H )‐furanone] across a 13‐membered macrocycle, a ( Z )‐trisubstituted olefin, and a five‐membered trans ‐fused cyclic ketal. The structure of 1 was resolved by interpretation of 1D and 2D NMR spectroscopic data supported by HRFAB‐MS, IR, UV, and a single‐crystal X‐ray diffraction analysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)