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.
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|
|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|
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