P-40 加水分解酵素の物質変換機能を基盤とする生理活性を有するデカリン型テルペン類の合成(ポスター発表の部)

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The optical resolution of racemic albicanol (rac-1) and racemic ketal (rac-2) were performed based on the lipase-catalyzed transesterification. The enzymetic resolution of rac-1 by using lipase QL and vinyl myristate as acyl donor afforded (-)-1 (99% ee) in 43% yield and (+)-1 (99% ee) in 37%, respectvely. The enzymetic resolution of rac-2 by using lipase QL and vinyl acetate afforded (-)-2 (99% ee) in 43% yield and (+)-2 (99% ee) in 37%, respectively. As the purpose of synthetic application of obtained optically active 1 and 2, several natural terpens were synthesized. (+)-Austrochaparol ((+)-3), (+)-cornarin E ((+)-4), (+)-cornarin A ((+)-5) and (+)-albaconol ((+)-6) were synthesized from (+)-1. The absolute configurations of (+)-3 and (+)-6 were determined to be 8aS by the comparison of their specific rotation between natural product and synthetic product. (-)-Copalic acid ((-)-7) possessing antimicrobial activity and (-)-copalol ((-)-8) were synthesized from (-)-1. (+)-Totarol ((+)-12) possessing antimicrobial activity against MRSA, (+)-podototarin ((+)-13), and (+)-sempervirol ((+)-14) were synthesized from (+)-2 based on Michael addition of β-ketoesters to α,β-unsaturated ketone ((8aS-17). The first total synthesis of (+)-jolkinolide D ((+)-15) that were known to induce apoptosis in tumor cells and (+)-jolkinolide E ((+)-16) were achieved from (-)-2.
天然有機化合物討論会の論文
2008-09-01