Efficiency and selectivity are two major goals in current organic synthesis and medicinal chemistry. Many natural products co-exist with their homologs and diastereomers, thus a highly efficient approach should be efficient not only for the concise synthesis of one member but also allowed accessing other homologs and diastereomers of the same family. Endophytic fungi constitute a rich source of bioactive natural products. (-)-Chaetominine11 (1, Fig. 1) was first isolated from an endophytic fungus on apparently healthy Adenophora axilliflora leaves. Following its isolation in 2006, the isolation of several homologs and diastereomers of chaetominine from different fungi have been reported. We report herein a unified strategy for the enantioselective total syntheses of all members of chaetominine natural products. The approach is highly efficient allowing access to 2-3 natural products in a single 4-6-step synthetic sequence.

Unified strategy for step-economical and enantioselective total synthesis of all members of chaetominine natural products

256th National Meeting (2018)

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