Journal
TETRAHEDRON LETTERS
Volume 52, Issue 38, Pages 4961-4964Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.07.079
Keywords
Total synthesis; Diastereoselective Diels-Alder reaction; Structure determination; PI-PLC inhibitor
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Funding
- Japan Society for the Promotion of Science [22390004]
- Grants-in-Aid for Scientific Research [22790023, 22390004] Funding Source: KAKEN
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We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1' position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin. (C) 2011 Elsevier Ltd. All rights reserved.
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