47(P04) 2-アリール-1,3-プロパンジオールの生理活性天然物合成への活用(ポスター発表の部)

概要

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A novel method for the construction of benzylic asymmetric tertiary and quaternary carbon centers, which were frequently found in biologically important natural products, has been developed. The methodology features the use of lipase-mediated asymmetric acetylation of σ-symmetrical prochiral 2-aryl-1,3-propanediols 1 for assembling the tertiary centers 2 and subsequent [1,5]C-H insertion reaction of alkylidene carbenes 3 on the generated asymmetric tertiary carbon for creating the quaternary centers 4. The syntheses of some biologically interesting natural products, i.e. aromatic bisabolene-type sesquiterpenoids, xanthorrhizol 14 and heliannuol D19, indolmycin 29, and ent-aflatoxin B_2 37 have been demonstrated by employing the benzylic asymmetric tertiary carbon construction methodology. Additionally, the synthesis of a potential intermediate for the synthesis of Calabar bean alkaloids, physostigmine 47 and physovenine 48, has been accomplished by using the quaternary center assembly.
天然有機化合物討論会の論文
1997-07-20