(+)-Dimericbiscognienyne A: Total Synthesis and Mechanistic Investigations of the Key Heterodimerization

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The first total synthesis of (+)-dimericbiscognienyne A is described. Key to the successful access to (+)-dimericbiscognienyne A was a biosynthetically inspired Diels-Alder reaction between two differential epoxyquinoid monomers and the subsequent intramolecular hemiacetal formation. The selective formation of the natural product among other possible diastereomers during the late-stage [4+2] cycloaddition reaction was investigated by DFT calculations and experimental control studies.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-10
Language
English
Article Type
Article
Keywords

EFFECTIVE CORE POTENTIALS; SOLVATION FREE-ENERGIES; MOLECULAR CALCULATIONS; EPOXYQUINOL-A; (+/-)-TORREYANIC ACID; DIMER; DENSITY; HYDROGEN; SKELETON

Citation

ORGANIC LETTERS, v.20, no.21, pp.6886 - 6890

ISSN
1523-7060
DOI
10.1021/acs.orglett.8b03025
URI
http://hdl.handle.net/10203/246513
Appears in Collection
CH-Journal Papers(저널논문)
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