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Oxa Bowls: Studies Toward Hexaoxa-[6]-peristylane.Synthesis of a Seco-Derivative of Hexaoxa-[6]-peristylane

Mehta, Goverdhan and Vidya, Ramdas (2001) Oxa Bowls: Studies Toward Hexaoxa-[6]-peristylane.Synthesis of a Seco-Derivative of Hexaoxa-[6]-peristylane. In: Journal of Organic Chemistry, 66 (21). pp. 6913-6918.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo010223n

Abstract

When the concept of equivalency of all-cis-[n]-formyl-[n]cycloalkanes with [n]-oxa-[n]-peristylanes was followed, an approach to the oxa bowl hexaoxa-[6]-peristylane 4a was delineated. This required an access to all-cis-cyclohexane-hexacarbaldehyde 5, which could be subjected to a 6-fold intramolecular acetalization cascade. A readily available Diels-Alder adduct of cyclooctatetraene and maleic anhydride was chosen as the starting material and was elaborated to the endo, endo-tetraene 6 in which all the six aldehyde functionalities are present in a latent form with cis orientation in a locked cyclohexane ring. Although ozonolysis of 6 has so far led only to intractable products, the novelty and brevity of our approach have been demonstrated through the intramolecular acetalizations through ozonolysis in 7 and 15, leading to oxa bowls 9 (seco-hexaoxaperistylane) and 16, respectively. The formation of 9 and 16 requires the generation of five tetrahydrofuran and four oxacyclic rings, respectively, in a single-pot operation.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to American Chemical Society.
Keywords: Oxa Bowls;Hexaoxa;peristylane;Synthesis;Seco-Derivative;Hexaoxa;peristylane
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Aug 2008
Last Modified: 19 Jan 2012 06:05
URI: http://eprints.iisc.ernet.in/id/eprint/2679

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