Total Synthesis of Biologically Active Compounds Based on the the Cascade-Type Sigmatropic Rearrangements

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Development of the cascade-type sigmatropic rearrangements of chiral allylic vicinal diol compounds which generates new C-C or C-N bonds via chirality transfer of C-O bonds of the substrate has been investigated. Biologically active compounds such as morphine and agelastatin A were successfully synthesized using the cascade-type Claisen and Overman rearrangements. The orthoamide-type Claisen and Overman rearrangements, which required no protecting group manipulation, were also developed. Based on the orthoamide-type rearrangement, effective total syntheses of kainic acid and broussonetine F were achieved.