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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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
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
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.ac.in/id/eprint/2679

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