Synthesis of complex furan building blocks via combined biocatalytic desymmetrizations and transition metal catalyzed cyclizations

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Based on our recent success in the lipase-mediated desymmetrization of prochiral allenes and glutarates, respectively, this research program deals with the linkage of bio- and metal catalyzed transformations in the context of modern organic synthesis. The interplay of chirality-creating desymmetrizations and complexity-creating cyclizations will serve as foundation for development of elegant and streamlined routes for the preparation of valuable synthetic building blocks. Here, the design of tailor-made functionalized enzyme substrates offers the immediate connection of a classical biocatalytic method with modern transition metal mediated reactions. The focus of our efforts lies in two complementary subprojects - the cycloisomerization of allenes and the (2,3)- sigmatropic oxonium-ylide rearrangement of allyl ethers - aiming for the development of efficient routes towards 2,4- and 2,5-disubstituted furan building blocks, respectively. To emphasize the synthetic benefit of these reaction sequences, the preparation of furan based natural products represents a vital part of the program.