Synthetic Studies on Spirolides A and B: Formation of the Upper Carbon Framework Based on a Lewis Acid Template-Catalyzed Diels–Alder Reaction |
| |
| Authors: | Prof Jun Ishihara Fuma Usui Tomohiro Kurose Tomohiro Baba Yasunori Kawaguchi Yuki Watanabe Prof Susumi Hatakeyama |
| |
| Institution: | 1. Graduate School of Biomedical Sciences, Nagasaki University, 1–14, Bunkyo-machi, Nagasaki, 852-8521 Japan;2. Medical Innovation Center, Nagasaki University, 1–14, Bunkyo-machi, Nagasaki, 852-8521 Japan |
| |
| Abstract: | The upper fragment of spirolides A and B, which are marine phycotoxins that exhibit strong antagonistic activities on nicotinic acetylcholine receptors, was constructed. The functionalized cyclohexene in spirolides was stereoselectively synthesized from the bicyclic lactone, which could be readily accessed by the Lewis acid template-catalyzed asymmetric Diels–Alder reaction of the pentadienol and methyl acrylate. |
| |
| Keywords: | catalytic reaction Diels–Alder reaction Lewis acids natural products spiro compounds stereoselective reactions |
|
|
