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Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC |
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| Authors: | Hayato HosoiNobuyuki Kawai Hideki HagiwaraTakahiro Suzuki Atsuo NakazakiKen-ichi Takao Kazuo UmezawaSusumu Kobayashi |
| Affiliation: | a Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan b Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
| Abstract: | 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. |
| Keywords: | Total synthesis Diastereoselective Diels-Alder reaction Structure determination PI-PLC inhibitor |
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