62(PA2-2) ポリエーテル系抗生物質イソラサロシドAとラサロシドAの合成研究(ポスター発表の部)
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概要
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The stereoselective synthesis of tetrahydrofurans and -pyrans has the key to success in the total synthesis of polyether antibiotics. We have planned a stereoselective synthesis of tetrahydrofurans and -pyrans, the acid-catalyzed cyclization of p-methoxystyryl derivertives. Several advantages of this cyclization are as follows. 1). p-Methoxystyryl derivertives (1, 4, 7, 9) are ready to be prepeared in an optically active form. 2). The cyclization proceeds smoothly under very mild conditions 3). The p-methoxystyryl group in the products was readily converted to the aldehyde group, which was favorable to further elabolations. This methodology was successfully applied for the synthesis of Isolasalocid A and Lasalocid A, that is, 1). Treatment of 1 with CSA gave only the trans product 15. This stereoselectivity was explained by considering a steric repulsion between acetonide and p-methoxystyryl groups. (Scheme 2) 2). The cyclization of 4 afforded 23 stereoselectively in good yield. The configration of 23 will be confirmed by the conversion of 23 to isolasalocid ketone 5. (Scheme 4) 3). Zinc bromide also affected this cyclization and compound 7 cyclized to 29 with high stereoselectivity (14: 1), which was explained in terms of the chelation by a zinc cation as shown in Fig.1. (Scheme 5) 4). The cyclization of 9 afforded 31 stereoselectively in good yield. The configration of 31 will be confirmed by its conversion to lasalocid ketone 10. (Scheme 6)
- 天然有機化合物討論会の論文
- 1987-07-25
著者
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及川 裕二
Faculty Of Pharmaceutical Sciences Hokkaido University
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米光 宰
岡山理大理
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米光 宰
Faculty of Pharmaceutical Sciences, Hokkaido University
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及川 裕二
北大薬
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米光 宰
北大薬
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米光 宰
Faculty Of Pharmaceutical Sciences Hokkaido University
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野田 一生
Faculty of Pharmaceutical Sciences, Hokkaido University
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堀田 清
北大薬
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野田 一生
北大薬
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堀田 清
Faculty Of Pharmaceutical Sciences Health Science University Of Hokkaido
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野田 一生
Faculty Of Pharmaceutical Sciences Hokkaido University
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