A Short Synthesis of (−)‐6,7‐Secoagroclavine via Metal‐Free Reductive Coupling

Abstract

AbstractA concise, convergent, and enantioselective synthesis of (−)‐6,7‐secoagroclavine, a pivotal intermediate in the synthesis of both clavine and ergot alkaloids, was accomplished from a derivative of the renowned Uhle's ketone. The synthesis is centered on metal‐free reductive coupling of the tosylhydrazone derivative of protected 4‐amino Uhle's ketone and commercially available 2,2‐dimethylethenylboronic acid, which is used as a four‐carbon building block. This novel approach directly sets the stereochemistry on the difficult‐to‐access aryl vinyl methane carbon stereogenic center of (−)‐6,7‐secoagroclavine.