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Synthesis Of (+/-)-2-Isopropyl-5,6-Dimethylbicyclo[3.2.1]Oct-6-En-8-One

Kasturi, TR and Chandra, R (1991) Synthesis Of (+/-)-2-Isopropyl-5,6-Dimethylbicyclo[3.2.1]Oct-6-En-8-One. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 30 (7). 639 -642.

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

Abstract

Methanolic hydrogen chloride cyclization of the triketone 8, prepared from the Mannich base 7 and 2-methylcyclopentane-1,3-dione, gives ketones 9 and 10. NaBH4 reduction of 9 followed by Grignard reaction with CH3MgI affords the diol 12. Catalytic hydrogenation of 12 followed by PCC oxidation yields the ketoalcohol 13. Dehydration of 13 with SOCl2/pyridine results in a 1:1 mixture of the endo-14 and exo-15 olefins, separated by chromatography.

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: 14 Dec 2010 05:28
Last Modified: 14 Dec 2010 05:28
URI: http://eprints.iisc.ernet.in/id/eprint/34196

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