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This article describes a design and synthesis of new and versatile chiral building blocks and its application to the biologically active natural product synthesis. The chiral building blocks were prepared using a biocatalysis in an enantiomerically 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, prosafrinine, iso-6-cassine, prosophylline, prosopinine, and also established the flexible route to the 5,8-disubstituted indolizidine or 1,4-disubstituted quinolizidine type of Dendrobates alkaloids. As another application to the synthesis of biologically active alkaloids, we accomplished the first 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 first total synthesis of a marine alkaloid lepadin B was also achieved using aldol cyclization controlled by a A strain.

Synthesis and Its Application to the Synthesis of Biologically Active Natural Products of New and Versatile Chiral Building Blocks