The ABC ring of LSD is a key scaffold of many ergot alkaloids and many pharmaceutically relevant neuromodulators. Previously, access to this scaffold was attained by sequentially synthesizing a substituted indole, followed by closure of the C-ring. In this work, the ABC-ring scaffold is synthesized from a structurally simple benzyl stannane and propargyl acid chloride via a one-pot Stille-Heck tandem coupling. The D ring is assembled via an inverse electron demand Diels-Alder reaction that allows for simple derivatization. Photoreactive derivatives of LSD are then evaluated for bioactivity and selectivity against dopamine and serotonin receptors for potential use as biased photoaffinity ligands.

Rapid assembly of the ABC-ring of LSD from propargyl acid chlorides and 2-halo-3-acetamido-benzyl stannanes via domino coupling and ring closure

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ACS Fall 2022

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