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.
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 $[220.127.116.11^2,^6]$decane system from which cis-hydrindane and cyclohexanoid moieties are sequentially extracted. The strategy outlined here exploits the propensity of the endo-tricyclo $[18.104.22.168^2,^6]$ 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|
|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|
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