Formal Syntheses of Naturally Occurring Welwitindolinones

The formal syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, N-methylwelwitindolinone D isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate, and 3-hydroxy-N-methylwelwitindolinone C isonitrile are reported. The synthesis features several novel...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 15; pp. 3834 - 3837
Main Authors Fu, Tsung-hao, McElroy, William T, Shamszad, Mariam, Martin, Stephen F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2012
Amer Chemical Soc
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Lewis Acids - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
METHYLWELWITINDOLINONE-C ISOTHIOCYANATE
CARBON SKELETON
CONSTRUCTION
MULTIPLE-DRUG RESISTANCE
ISONITRILE
CHLORIDES
WELWISTATIN
BETA-KETO-ESTERS
EFFICIENT
OXIDIZED WELWITINDOLINONES
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Summary:The formal syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, N-methylwelwitindolinone D isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate, and 3-hydroxy-N-methylwelwitindolinone C isonitrile are reported. The synthesis features several novel processes, including a Lewis acid mediated coupling between a benzylic-type heteroaromatic alcohol and a highly functionalized silyl ketene acetal, an intramolecular enolate arylation, and a regioselective, Pd(0)-catalyzed π-allylic cyclization of a γ-benzoyloxy enone moiety that is revealed by unmasking a furan ring.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol301424h