Pauson-Khand Reaction on the 1,2-Isopropylidenedioxyfuranoside Scaffold: Expedient Access to a Chiral Cyclopenta[c]pyran Ring System
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Pauson-Khand Reaction on the
1,2-Isopropylidenedioxyfuranoside
Scaffold: Expedient Access to a Chiral Cyclopenta[c]pyran Ring System
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| Creator |
Pal, Arani
Bhattacharjya, Anup |
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| Subject |
Chemistry
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| 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 of
irridoids such as loganin, iridomyrmecin ,and boschnialactone.
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| Date |
2001
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/888/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C__66(_26)%2C_9071%2D9074[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. Journal Of Organic Chemistry, 66 (26). pp. 9071-9074. |
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| Relation |
http://dx.doi.org/10.1021/jo015955u
http://www.eprints.iicb.res.in/888/ |
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