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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Published inChemical communications (Cambridge, England) Vol. 51; no. 22; pp. 4576 - 4578
Main Authors Huang, Pei-Qiang, Huang, Su-Yu, Gao, Long-Hui, Mao, Zhong-Yi, Chang, Zong, Wang, Ai-E
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.03.2015
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Chemistry
Chemistry, Multidisciplinary
Construction
Crystallography, X-Ray
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Strategy
Synthesis
CORE
SEMISYNTHESIS
ASYMMETRIC-SYNTHESIS
STEMOFOLINE
DIPOLAR CYCLOADDITION
CONVERSION
INTERMOLECULAR ADDITION-REACTIONS
CONSTRUCTION
CHEMISTRY
ALKALOIDS
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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 2 with an E-alkene, and its absolute configuration was established.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc09598g