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Ciereszkolide: Isolation and Structure Characterization of a Novel Rearranged Cembrane from the Caribbean Sea Plume Pseudopterogorgia kallos

✍ Scribed by Jeffrey Marrero; Abimael D. Rodríguez; Peter Baran; Raphael G. Raptis

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 113 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200400292

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✦ Synopsis

Abstract

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)

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