An efficient synthesis of diquinane-based bis-γ-lactones

Khan, FaizAhmed ; Nageswara Rao, Ch. (2006) An efficient synthesis of diquinane-based bis-γ-lactones Tetrahedron Letters, 47 (43). pp. 7567-7570. ISSN 0040-4039

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An efficient stereoselective synthesis of both the diastereomers of diquinane-based conformationally constrained symmetric bis-γ-lactones starting from tricyclic derivative 9 is reported. The key step involves the intramolecular ring opening of an epoxide by the in situ formed hydrate of a diketone leading to the tetracyclic hemiacetal 10, which directly leads to the exo-hydroxy bis-γ-lactone derivatives 2 and 4 under basic hydrogen peroxide cleavage conditions. Conversion to the endo-hydroxy bis-γ-lactone derivatives 1 and 3 was accomplished through lithium hydroxide mediated SN2 displacements in dimesylate 7, or more expeditiously, via trimesylate 21 through alkaline H2O2 mediated cleavage.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:80325
Deposited On:31 Jan 2012 14:27
Last Modified:31 Jan 2012 14:27

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