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Pauson-Khand Reaction on the 1,2- Isopropylidenedioxyfuranoside Scaffold: Expedient Access to a Chiral Cyclopenta[c]pyran Ring System

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Title Pauson-Khand Reaction on the 1,2- Isopropylidenedioxyfuranoside Scaffold: Expedient Access to a Chiral Cyclopenta[c]pyran Ring System
 
Creator Pal, Arani
Bhattacharjya, Anup
 
Subject Chemistry
 
Description The Pauson-Khand reaction (PKR) has been established
as a powerful method for the synthesis of cyclopentenone
derivatives by way of union of an alkene and alkyne moieties in the presence of dicobaltoctacarbonyl
and other related metal species.1 The intramolecular
variety of the reaction has gained much popularity
because it can furnish cyclopentenone-fused ring systems,
which are otherwise difficultly accessible. Although the
utility of this useful reaction in the construction of chiral ring skeletons has been well documented, its application to the carbohydrate template for the purpose is relatively recent.1,2 The majority of such reactions using carbohydrate derivatives have been reported for pyranoside rings with on-template ene systems.2 Recent reports from our
laboratory have demonstrated the utility of the 1,2-
isopropylidenedioxyfuranside ring system as a potentially
useful scaffold for carrying out cycloaddition reactions.3a-f The important features of this scaffold are the ready availability of the starting material, easy characterizability of the products, and the scope of further transformations of the products giving rise to diverse types of molecules. Herein, we describe a brief study on the PKR of enyne systems built on the 1,2-isopropylidenedioxyfuranoside scaffold leading to the chiral cyclopenta[c]-pyran skeleton, which constitutes the frameworks ofirridoids such as loganin, iridomyrmecin ,and boschnialactone. 4
 
Publisher American Chemical Society
 
Date 2001
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2324/1/JOURNAL_OF_ORGANIC_CHEMISTRY__V._66__(_26_)_9071%2D9074;_2001[1].pdf
Pal, Arani and Bhattacharjya, Anup (2001) Pauson-Khand Reaction on the 1,2- Isopropylidenedioxyfuranoside Scaffold: Expedient Access to a Chiral Cyclopenta[c]pyran Ring System. The Journal of Organic Chemistry, 66 (26). pp. 9071-9074.
 
Relation http://dx.doi.org/10.1021/jo015955u
http://www.eprints.iicb.res.in/2324/