P-40 Pd触媒による六員環形成反応を用いたピペリジンアルカロイド(-)-cassin,spectamin Aおよびバンレイシ科アセトゲニンpyranicinの合成研究(ポスター発表の部)

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Palladium-catalyzed stereoselective cyclization of alkenylamine and alkenylalcohol is very important methodologies for the stereoslective construction of oxygen and nitrogen hetero alicycles. In this symposium, we wish to present Pd-catalyzed diastereoselective N- and O-alkylation and their application for natural products. 1. Synthesis of (-)-cassine (1) A number of the piperidine alkaroids, especially 2,6-disubstituted piperidin-3-ols, have been found abundantly in nature, and many of them show interesting pharmacological activities. We have developed the Pd catalyzed cyclization to give piperidine 9 with excellent diastereoselectivity. The versatility of compound 9 as the building block for synthesizing cis-2, 6-disubstituted piperidine alkaloids has been demonstrated by a total synyhesis of (-)-cassine (1). 2. Synthetic studies on spectamine A (2) Recently, we have isolated a novel piperidine alkaroids from an African legume, Cassia spectabilis, and identified as O-benzoyl [spectamine A (2)] derivatives of (+)-iso-6-Cassine. Herein we wish to report the progress toward synthesis of 2 using Pd catalyzed stereoselective cyclization to give 2, 6-trans-piperidine ring 16t. Total synthesis of 2 is currently underway. 3. Synthetic studies on pyranicin (3) Synthetis studies on pyranicin (3), isolated from Annonaceae, is described. The THP ring moiety was constructed using Pd catalyzed stereoselective cyclization. Total synthesis of 3 is now underway.
天然有機化合物討論会の論文
2006-09-15

P-40 Pd触媒による六員環形成反応を用いたピペリジンアルカロイド(-)-cassin,spectamin Aおよびバンレイシ科アセトゲニンpyranicinの合成研究(ポスター発表の部)

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