Mehta, Goverdhan and Reddy, Srinivasa D (2000) A formal synthesis of reserpine: hydrindane approach to the Woodward’s ring-E precursor. In: Journal of Chemical Society: Perkin Transactions 1 . pp. 1399-1404.
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Abstract
A new synthetic approach to a functionally and stereochemically embellished cyclohexanoid, corresponding to the Woodward’s ring-E intermediate 24 of the complex indole alkaloid reserpine 1 is delineated. Our scheme emanates from a readily available endo-tricyclo $[5.2.1.0^2,^6]$decane system from which cis-hydrindane and cyclohexanoid moieties are sequentially extracted. The strategy outlined here exploits the propensity of the endo-tricyclo $[5.2.1.0^2,^6]$ decane and cis-hydrindane systems to react from the convex face to generate the requisite stereochemical pattern. Since 24 has been previously elaborated to the natural product, the present effort constitutes a formal synthesis of rac-reserpine.
Item Type: | Journal Article |
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Publication: | Journal of Chemical Society: Perkin Transactions 1 |
Publisher: | The Royal Society of Chemistry |
Additional Information: | Copyright for this article belongs to The Royal Society of Chemistry. |
Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
Date Deposited: | 24 Jan 2005 |
Last Modified: | 19 Sep 2010 04:17 |
URI: | http://eprints.iisc.ac.in/id/eprint/2696 |
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