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Synthetic studies towards pteridanone, a novel protoilludane-type tricyclic sesquiterpenoid

Mehta, Goverdhan and Ghosh, Partha and Sreenivas, Katukojvala (2003) Synthetic studies towards pteridanone, a novel protoilludane-type tricyclic sesquiterpenoid. In: ARKIVOC (Part i). pp. 176-187.


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A synthetic approach directed towards the total synthesis of the novel protoilludane sesquiterpene pteridanone, the aglycon of the glucoside pteridanoside from a bioactive hot-water extract of the neotropical braken fern Pteridium aquilinum var. caudatum (Dennstaedtiaceae), has been delineated. This endeavour has delivered an advanced pre-target having the complete protoilludane skeleton with strategic placement of the functionalities and set the stage for the total synthesis of the natural product. The key features of our approach are the ready availability of the starting material (1,5-cyclooctadiene), an interesting photochemical [2+2]-cycloaddition and a thallium(III) mediated ring expansion reaction.

Item Type: Journal Article
Publication: ARKIVOC
Publisher: ARKAT USA
Keywords: Sesquiterpenes;[2+2]-photocycloaddition;ring expansion;Wittig reaction
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Aug 2008
Last Modified: 19 Sep 2010 04:17
URI: http://eprints.iisc.ac.in/id/eprint/2666

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