Journal
ACS CATALYSIS
Volume 12, Issue 24, Pages 14990-14998Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c04076
Keywords
desymmetrization; carbene; metal catalyst; biocatalyst; asymmetric reaction
Categories
Funding
- Futaba Electronics Memorial Foundation
- Ube Industries Foundation
- Sumitomo Foundation
- Suzuken Memorial Foundation
- Research Foundation for Pharmaceutical Sciences
- JSPS-DAAD (DAAD) [57458216]
- JSPS KAKENHI [22H02741, G21K06471, 20J20933]
- Digitalization-driven Trans-formative Organic Synthesis [22H05337]
- Chiba University SEEDS Fund
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This study reported a catalytic approach for the formal synthesis of more than 20 types of sarpagine/macroline alkaloids, with two key steps being the amide insertion reaction using cheap copper and biocatalytic asymmetric desymmetrization.
Although the molecular structural motif of indole-fused azabicyclo[3.3.1]nonane is common in biologically significant natural products, its catalytic asymmetric synthesis remains underexplored. Herein, we report a catalytic approach for the formal synthesis of more than 20 types of sarpagine/macroline alkaloids. Two key steps are the amide insertion reaction using a metalcarbene species based on cheap copper and biocatalytic asymmetric desymmetrization, producing the desired chiral N -bridged [3.3.1] scaffold. The enzymatic step proceeds highly enantioselectively when using lipase from Candida rugosa, which turned out to be the best for breaking the symmetry. Late-stage introduction of an indole unit with functionalities then established a diversity oriented synthetic pathway toward indole terpenoid variants.
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