Journal
ORGANIC LETTERS
Volume 21, Issue 20, Pages 8485-8487Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03319
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Funding
- Key Research Program of the Frontier Sciences of the CAS [QYZDB-SSW-SMC026, ZDBS-LY-SM030]
- NSFC [21672224, 21971249]
- Government of Yunnan Province [2017FA002]
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A catalytic, enantioselective formal synthesis of monoterpene indole alkaloid (-)-alstoscholarine is described. The synthesis employs an Ir-amine dual catalyzed asymmetric allylation of aldehyde 8 with 3-indolyl vinyl carbinol derivative 7 to furnish chiral aldehyde 6 as a key asymmetric step. Other key reactions include the construction of the 2-ketopyrrole moiety by Nicolaou's method and Tf2O promoted Pictet Spengler cyclization to access Zhu's intermediate 3.
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