Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products

The formal syntheses of N-methylwelwitindolinone C isothiocyanate (4) and several other welwitindolinones 5–8 were achieved by the independent synthesis of 79. The synthesis featured a Lewis acid-mediated coupling between a heteroaryl carbinol and bis-TMS enol ether, an intramolecular enolate arylat...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 27-28; pp. 5588 - 5603
Main Authors Fu, Tsung-hao, McElroy, William T., Shamszad, Mariam, Heidebrecht, Richard W., Gulledge, Brian, Martin, Stephen F.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.07.2013
Elsevier
Subjects
Alkaloids
Alkylation
Allylic alkylation
Chemistry
Chemistry, Organic
Enolate arylation
Ethers
Joining
Lewis acid-mediated coupling
Natural products
Physical Sciences
Science & Technology
Synthesis
Tetrahedrons
Welwitindolinones
Alkaloids
Allylic alkylation
Enolate arylation
Lewis acid-mediated coupling
Welwitindolinones
VINYL CHLORIDES
SUBSTITUTION
ASYMMETRIC-SYNTHESIS
FURANS
EFFICIENT SYNTHESIS
WELWISTATIN
KETONES
CONSTRUCTION
STEREOSELECTIVE-SYNTHESIS
OXIDIZED WELWITINDOLINONES
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Summary:The formal syntheses of N-methylwelwitindolinone C isothiocyanate (4) and several other welwitindolinones 5–8 were achieved by the independent synthesis of 79. The synthesis featured a Lewis acid-mediated coupling between a heteroaryl carbinol and bis-TMS enol ether, an intramolecular enolate arylation, and an unprecedented intramolecular allylic alkylation of a γ-acyloxyenone. [Display omitted]
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.03.010