Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 18, Pages 11968-11974Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01660
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Funding
- NSFC [21871117, 21672145, 21502080, 91956203]
- STCSM [17JC1403700]
- Ministry of Science and Technology of China (Drug Innovation Major Project) [2018ZX09711001-005-002]
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Previously, we have finished the total synthesis of lycojaponicumin A (2) via development of an efficient synthetic strategy using semipinacol rearrangement as a key step. In order to further demonstrate the generality of this synthetic route, herein, we report the total synthesis of another fawcettimine-type alkaloid sieboldine A (1) from the same intermediate, which possesses an A/B/D tricyclic ring system and vicinal quaternary centers of 1. The synthesis features late-stage site-selective redox reactions, Schmidt glycosylation cyclization, and highly selective transformations.
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