A Radical-Polar Crossover Annulation To Access Terpenoid Motifs

A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskoli...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 31; pp. 12246 - 12250
Main Authors Thomas, William P, Schatz, Devon J, George, David T, Pronin, Sergey V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2019
Amer Chemical Soc
Subjects
carbonyl compounds
catalytic activity
Chemistry
Chemistry, Multidisciplinary
Colforsin - chemical synthesis
Colforsin - chemistry
forskolin
Physical Sciences
Science & Technology
Stereoisomerism
Terpenes - chemistry
CYCLASE
HYDROGENATION
DIELS-ALDER REACTIONS
SPONGE
CYCLOADDITIONS
COMPLEXES
FORSKOLIN
UNACTIVATED ALKENES
FE
SESTERTERPENES
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Summary:A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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Present Address D.T.G.: Bristol-Myers Squibb, New Brunswick, NJ 08901
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b07346