A Concise Approach to Paxilline Indole Diterpenes

A synthetic approach to paxilline indole diterpenes is described. The route to the penta­cyclic core relies on a new regio­selective alkenyl­ation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereo­centers. Emindole SB, the simplest member of the fam...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 49; pp. 15410 - 15413
Main Authors George, David T, Kuenstner, Eric J, Pronin, Sergey V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Diterpenes - chemistry
diterpenoids
Indoles - chemistry
ketones
Molecular Structure
paxilline
Physical Sciences
Science & Technology
Terpenes - chemistry
TERTIARY ALCOHOLS
ENOL ETHERS
BIOSYNTHESIS
CONSTRUCTION
ALPHA
QUATERNARY CARBONS
2ND-GENERATION SYNTHESIS
CONJUGATE ADDITION
CARBOXYLIC-ACIDS
ALKALOIDS
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Summary:A synthetic approach to paxilline indole diterpenes is described. The route to the penta­cyclic core relies on a new regio­selective alkenyl­ation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereo­centers. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b11129