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- Title
The Synthesis and Biological Evaluation of Desepoxyisotedanolide and a Comparison with Desepoxytedanolide.
- Authors
Naini, Arun; Muthukumar, Yazh; Raja, Aruna; Franke, Raimo; Harrier, Ian; Smith, Amos B.; Lee, Dongjoo; Taylor, Richard E.; Sasse, Florenz; Kalesse, Markus
- Abstract
The tedanolides are biologically active polyketides that exhibit a macrolactone constructed from a primary alcohol. Since polyketidal transformations only generate secondary alcohols, it has been hypothesized by Taylor that this unique lactone could arise from a postketidal transesterification. In order to probe this hypothesis and to investigate the biological profile of the putative precursor of all members of the tedanolide family, we embarked on the synthesis of desepoxyisotedanolide and its biological evaluation in comparison to desepoxytedanolide. The biological experiments unraveled a second target for desepoxytedanolide and provided evidence that the proposed transesterification indeed provides a survival advantage for the producing microorganism.
- Subjects
POLYKETIDES; CHEMICAL synthesis; INVERTEBRATE sponge physiology; CRYSTAL structure; MARINE microorganisms; TRANSESTERIFICATION
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 23, p6935
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201501526