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Wang, Pengyan; Chen, Junhan; He, Weigang; Song, Jiacheng; Song, Hengqian; Wei, Hongbo; Xie, Weiqing
Organic letters, 07/2021, Letnik: 23, Številka: 14Journal Article
Herein, a concise asymmetric synthesis of (+)-isostrychnine is achieved in nine longest-linear steps with a 16% overall yield. The key features of this synthesis include the catalytic asymmetric tandem double Michael addition of a tryptamine-derived oxindole to an alkynone to facilely forge the A/B/C ring framework, a one-pot intramolecular dehydrative condensation/lactamization reaction to efficiently establish the E/G ring system, and an allylic diazene rearrangement to introduce the pivotal olefin for the subsequent intramolecular Heck reaction.
