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The Total Synthesis of (+)‐Tedanolide—A Macrocyclic Polyketide from Marine Sponge Tedania ignis
Author(s) -
Ehrlich Gunnar,
Hassfeld Jorma,
Eggert Ulrike,
Kalesse Markus
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701529
Subject(s) - polyketide , stereochemistry , sponge , chemistry , thioesterase , bioassay , biosynthesis , biology , biochemistry , enzyme , genetics , botany
Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis , is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations others than those derived by the thioesterase reaction. First experimental data that support this hypothesis and reflect the inherent preference of PKS‐induced macrolactonization were obtained during this synthesis. The inherent preference for the formation of a 14‐membered macrocyclization is discussed together with the pivotal steps in the synthesis.