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Stereochemistry of Antiinflammatory Marine Sesterterpenes
Author(s) -
Soriente Annunziata,
Crispino Antonio,
De Rosa Margherita,
De Rosa Salvatore,
Scettri Arrigo,
Scognamiglio Gennaro,
Villano Rosaria,
Sodano Guido
Publication year - 2000
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/(sici)1099-0690(200003)2000:6<947::aid-ejoc947>3.0.co;2-u
Subject(s) - chemistry , absolute configuration , stereocenter , stereochemistry , moiety , terpene , two dimensional nuclear magnetic resonance spectroscopy , enantioselective synthesis , organic chemistry , catalysis
The absolute configuration of antiinflammatory marine sesterterpenes belonging to the manoalide and cacospongionolide structural type has been determined by comparison of the CD spectra of the natural compounds with those of analogues that have been stereoselectively synthesized. In the derived acetates the relative stereochemistry of the stereogenic centres in the pyranofuranone moiety is assigned from 1 H‐NMR data and the absolute configuration from CD spectra. The absolute configuration of the naturally occurring marine sesterterpenes thorectolide monoacetate, manoalide monoacetate, petrosaspongiolide M and cavernosolide has been determined.