期刊
ORGANIC LETTERS
卷 23, 期 13, 页码 4981-4985出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01389
关键词
-
资金
- Tamaki Foundation
The synthesis of the pentacylic core of (+)-cit-rinadin A was described using palladium-catalyzed trimethylenemethane chemistry. The key spirooxindole motif was formed in a catalytic, asymmetric fashion, with subsequent addition of the piperidine ring and final ring formation through an intramolecular displacement reaction.
The synthesis of the pentacylic core of (+)-cit-rinadin A is described. Our strategy harnesses the power of palladium-catalyzed trimethylenemethane chemistry (Pd-TMM) to form the key spirooxindole motif in a catalytic, asymmetric fashion. Upon the conversion of this spirooxindole to a vinyl epoxide electrophile, the piperidine ring is directly added via a diastereoselective metalation followed by an S(N)2' addition. The final ring of the pentacyclic core is then formed through an intramolecular S(N)2 displacement of the resulting activated alcohol.
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