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Rearrangement of homobrendane derivatives. Total syntheses of racemic copacamphor, ylangocamphor, and their homologs

Kasturi, TR and Chandra, R (1988) Rearrangement of homobrendane derivatives. Total syntheses of racemic copacamphor, ylangocamphor, and their homologs. In: Journal of Organic Chemistry, 53 (14). pp. 3178-3183.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00249a010

Abstract

Rearrangement of a homobrendane derivative 8a to perhydro-1,4-methanoindenesy stem 9a could be brought about either by p-toluenesulfonic acid or boron trifluoride etherate. Similarly, rearrangement of 8b-d led to the formation of perhydro-1,4-methanoindened erivatives 9b-d. On the basis of the location of substituents in the starting material and the product, a probable mechanistic pathway has been suggested. The appropriate modification of the peripheral functionalities in 9 led to efficient total syntheses of (f)-copacamphor (15a),(f)-ylangocamphor (16a), and their homologues 15b and 16b.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 29 Sep 2010 10:01
Last Modified: 29 Sep 2010 10:01
URI: http://eprints.iisc.ernet.in/id/eprint/32530

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