Synthesis of highly functionalized δ-lactone-fused cyclopentanoids

Khan, Faiz Ahmed ; Krishnakumar, K. S. ; Sudheer, Ch. (2007) Synthesis of highly functionalized δ-lactone-fused cyclopentanoids Synthesis, 2007 (7). pp. 1054-1060. ISSN 0039-7881

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A short and efficient route to d-lactone-fused cyclopentanoids starting from the easily accessible Diels-Alder adducts between homoallylic alcohol acetates and 1,2,3,4-tetrachloro-5,5-dimethoxycyclopenta-1,3-diene is reported. Since homoallyl alcohols were derived from the corresponding aldehydes RCHO (R = alkyl, aryl) through allyl metal addition, the methodology is broad in scope with regard to the choice of R group. The initially formed 1:1 diastereomeric mixture of adducts were subjected to ruthenium-catalyzed oxidation followed by acid-mediated hydrolysis of the acetate groups to obtain the hemiacetals 6a-e. Alkaline H2O2-mediated cleavage of the hemiacetals led, after esterification with diazomethane, to a chromatographically separable diastereomeric mixture of 7 and 8 in high overall yield (54-68%).

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:δ-lactones; Diels-Alder Reactions; α-diketones; α-keto Hemiacetals; Diastereomers
ID Code:80346
Deposited On:31 Jan 2012 14:27
Last Modified:31 Jan 2012 14:27

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