Concise Syntheses of GB22, GB13, and Himgaline by Cross-Coupling and Complete Reduction
Ryan Shenvi presents a concise method for the synthesis of GB22, GB13, and himgaline.
Galbulimima (GB) is a genus of large, flowering tree that grows in tropical regions of eastern Asia and Oceania. GB bark finds use as an antipyretic, analgesic, and hallucinogenic by indigenous Papuans, although the alkaloid or alkaloids responsible for these responses remain unknown. The group of Professor Ryan Shenvi at Scripps Research (La Jolla, USA) has been working on this problem. Professor Shenvi explained that “due to the poor accessibility of GB trees, low natural abundance of alkaloids, and considerable variation between bark samples, chemical synthesis may be the best way to correlate alkaloid structure to biological function.” Access to class III GB alkaloids was significantly enhanced by strategic installation of methine stereocenters and a novel metallaphotoredox crosscoupling of aryl bromides and siloxycyclopropanes.
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