Total Syntheses of Perenniporides

The total syntheses of perenniporide A (1) and related compounds have been achieved. Starting from 1,3,5-trifluorobenzene (9), difluorodienone 6 was obtained by oxidative dearomatization, which served as a platform for the high-pressure cycloaddition and for the introduction of the C3-methoxy group....

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Published inOrganic letters Vol. 17; no. 22; pp. 5634 - 5637
Main Authors Morita, Masao, Ohmori, Ken, Suzuki, Keisuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2015
Amer Chemical Soc
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
chemical structure
Chemistry
Chemistry, Organic
Cycloaddition Reaction
cycloaddition reactions
Fluorobenzenes - chemistry
Molecular Structure
organic compounds
Oxidation-Reduction
Physical Sciences
Pressure
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
AROMATIC METALATION
OXIDATION
HIGH-PRESSURE
CARBON
ORTHODIRECTING GROUP
FLUORINE
ERYTHRINAN ALKALOIDS
CANTHARIDIN
ACCESS
DEAROMATIZATION
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.5b02906

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Summary:The total syntheses of perenniporide A (1) and related compounds have been achieved. Starting from 1,3,5-trifluorobenzene (9), difluorodienone 6 was obtained by oxidative dearomatization, which served as a platform for the high-pressure cycloaddition and for the introduction of the C3-methoxy group. The synthesis allowed access to the natural congeners 2 and 3, enabling assignment of the absolute structures of these natural products.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b02906