Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane

Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels–Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of α-brominated Diels–Alder adduct is...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-03, Vol.77 (5), p.2513-2518
Main Authors: Jung, Sun Hee, Hwang, Geum-Sook, Lee, Sung Il, Ryu, Do Hyun
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bromochlorofluorocarbons
Chemistry
Chlorofluorocarbons, Methane - chemistry
Cyclohexanones - chemical synthesis
Cyclohexanones - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels–Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of α-brominated Diels–Alder adduct is described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202357s