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Synthetic Studies Towards Prismanes - Rearrangements In Some Pentacyclic Precursors And X-Ray Crystal-Structure Of A Novel Heptacyclic Ether

Mehta, G and Venkatesan, K and Moorthy, JN and Begum, NS and Padma, S (1992) Synthetic Studies Towards Prismanes - Rearrangements In Some Pentacyclic Precursors And X-Ray Crystal-Structure Of A Novel Heptacyclic Ether. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 31 (8). pp. 473-482.

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Official URL: http://www.niscair.res.in/ScienceCommunication/Res...

Abstract

In order to gain access to the heptacyclic tetraone 3, efforts were directed towards the utilisation of the major 'unwanted' [4 + 2]-adduct 11 of tetrachlorodimethoxycyclopentadiene and norbornenobenzoquinone. Epoxides derived from the diol and dimethoxy derivatives of the adduct 11 undergo facile Wagner-Meerwein rearrangement resulting in the required endo, syn, endo stereochemistry as well as methano-bridge functionalisation to deliver 18 and 24, respectively. However, intramolecular ether formation, occurring via the capture of carbocation intermediate with the transannularly poised oxygen functionality, is a more facile process. Attempts to cleave the ether linkage resulted in the formation of a novel transannularly cyclised twisted bowl shape heptacyclic compound 30 and its structure has been established through X-ray crystallography.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 May 2011 05:57
Last Modified: 30 May 2011 05:57
URI: http://eprints.iisc.ernet.in/id/eprint/37763

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