A formal synthesis of reserpine: hydrindane approach to the Woodward’s ring-E precursor

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
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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