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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of (±)-Mersicarpine and Related Kopsia Alkaloids Frameworks via a Cyanomethyl Radical Addition/Cyclization
Carlos H Escalante1, Mario Castañón-García1, Luis D Miranda1
1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, Ciudad de México04510, México.
Abstract:
In this work, we report a concise, protecting-group-free, seven-step total synthesis of (±)-mersicarpine in 15% overall yield, from commercial γ-caprolactone, representing the shortest racemic route reported to date. In addition, formal synthetic approaches to rhazinilam and leuconoxine alkaloids were achieved. The strategy relies on a cyanomethyl radical cascade cyclization of N-alkene-linked indole and pyrrole substrates under either DLP-mediated or photoredox conditions, providing rapid access to key polycyclic frameworks.
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