Enantioselective total synthesis of (+)-methoxystemofoline and (+)-isomethoxystemofoline

The first enantioselective total synthesis of (+)-methoxystemofoline (2) and (+)-isomethoxystemofoline (3) has been reported. The synthesis employed the halide-assisted bromotropanonation method that we developed recently to construct the core structure, and Overman's strategy for the implement...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-03, Vol.51 (22), p.4576-4578
Main Authors: Huang, Pei-Qiang, Huang, Su-Yu, Gao, Long-Hui, Mao, Zhong-Yi, Chang, Zong, Wang, Ai-E
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Construction
Crystallography, X-Ray
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Models, Molecular
Molecular Structure
Stereoisomerism
Strategy
Synthesis
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Summary:The first enantioselective total synthesis of (+)-methoxystemofoline (2) and (+)-isomethoxystemofoline (3) has been reported. The synthesis employed the halide-assisted bromotropanonation method that we developed recently to construct the core structure, and Overman's strategy for the implementation of the butenolide moiety. Through this work, the structure of methoxystemofoline was revised as with an E-alkene, and its absolute configuration was established.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc09598g