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Short Synthesis of the Monoterpene Indole Alkaloid (±)-Arbornamine

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journal contribution
posted on 28.03.2018, 00:00 authored by Yu Zheng, Bei-Bei Yue, Kun Wei, Yu-Rong Yang
The first total synthesis of the monoterpene indole alkaloid (±)-arbornamine (1) has been completed, which proceeds in only 6 steps and 31% overall yield from three readily available, known compounds. The synthesis features a cascade involving a Pictet–Spengler cyclization/intramolecular ammonolysis to create the tetracyclic core of arbornamine (1) in a single chemical operation. The subsequent elaboration of 5 into 1 was effected by a key reductive Heck reaction and global reduction.