新规泛用性キラル素子の创制とその生物活性天然物合成への - j-stage.pdf

YAKUGAKU ZASSHI 121(7) 467―479 (2001) 467467 ―Reviews― 新規汎用性キラル素子の創製とその生物活性天然物合成への応用 豊 岡 尚 樹 富山医科薬科大学薬学部，〒  富山市杉谷 930 0194 2630 Synthesis and Its Application to the Synthesis of Biologically Active Natural Products of New and Versatile Chiral Building Blocks Naoki TOYOOKA  Toyama Medical and Pharmaceutical University, 2630, Sugitani, Toyama 930 0194, Japan （ ） Received March 8, 2001 This article describes a design and synthesis of new and versatile chiral building blocks and its application to the bio- logically active natural product synthesis. The chiral building blocks were prepared using a biocatalysis in an enantio- merically pure state. As an application of the above chiral building blocks to the synthesis of biologically active natural product, we demonstrated the diastereodivergent synthesis of the 3-piperidinol alkaloids cassine, spectaline, prosafri- nine, iso-6-cassine, prosophylline, prosopinine, and also established the ‰exible route to the 5,8-disubstituted indolizi- dine or 1,4-disubstituted quinolizidine type of Dendrobates alkaloids. As another application to the synthesis of biologi- cally active alkaloids, we accomplished the ˆrst enantioselective total synthesis of marine alkaloids clavepictines A, B, and pictamine using a highly stereoselective Michael type quinolizidine ring closure reaction as the crucial step, and the ˆrs