First total synthesis of (-)-AL-2 |
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Authors: | Miyakoshi Naoki Mukai Chisato |
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Institution: | Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan. |
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Abstract: | Treatment of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivative, derived from diethyl l-tartrate, with a palladium catalyst in methanol under a CO atmosphere effected an intramolecular acetalization and a stereoselective construction of the (E)-methoxycarbonylmethylidene functionality resulting in formation of the core framework of the diacetylenic spiroacetal enol ether natural products. Chemical transformations of the 1,6-dioxaspiro4.5]decane derivative thus formed led to the first total synthesis of (-)-AL-2. reaction: see text] |
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