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Novel strategy constructs chasmanine by using radical cyclization and vinylogous Mannich reactions, suggesting new synthetic pathways.
Chasmanine and puberuline C share a hexacyclic ABCDEF-ring but differ in the fusion pattern of their 5- and 6-membered F-rings. Here, we present a novel strategy for constructing the chasmanine skeleton, starting from a key intermediate employed in our total synthesis of puberuline C. Following optimization of a radical cyclization to build the ABCE-ring system, Hg(OAc) 2 -promoted vinylogous Mannich and Mukaiyama aldol reactions formed the F- and D-rings, respectively, thereby completing the assembly of the hexacycle.
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Asai et al. (2026) studied this question.
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