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SYNTHESIS OF NATURAL PRODUCT NEPETANUDONE THROUGH THERMALLY FORBIDDEN [4Π+4Π] CYCLOADDITION IN THE PRESENCE OF LIGHT

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abstract
The biosynthesis of different natural products have been proved or proposed to involve a number of photochemical reactions like photocyclizations, Norrish type reactions, photochemical rearrangements, reactions via dienol intermediates, Paterno-Buchi reaction, photodimerization, photo-claisen rearrangement etc [1]. These reactions have been used to either support the biosynthesis of these compounds or they provide an alternate and easy synthetic route. The natural product Nepetanudone was first isolated from extracts of the aerial parts of Nepeta parnassica. This compound is structurally similar to the natural product Nepetaparnone. They differ only in two stereo centers and both have significant biological and medicinal properties. Nepetanudone was proposed to be biosynthesized through the cycloadditon of two Nepetapyrones (5,9-dehydronepetalactone). This precursor pyrone was synthesized in the laboratory through six step reaction pathways as shown in Scheme 4. Once this compound was developed, it was photolyzed at different conditions and the formation of the products was monitored. By developing the Nepetanudone in the lab, as proposed, this work provide evidence for the biosynthesis of Nepetanudone through the photocycloaddition reaction of two 5,9-dehydronepetalactones.
subject
contributor
Jayan, Swapna (author)
Jones, Paul B (committee chair)
Jones, Amanda (committee member)
Bierbach, Ulrich (committee member)
date
2014-01-15T09:35:35Z (accessioned)
2014-07-15T08:30:09Z (available)
2013 (issued)
degree
Chemistry (discipline)
embargo
2014-7-15 (terms)
identifier
http://hdl.handle.net/10339/39138 (uri)
language
en (iso)
publisher
Wake Forest University
title
SYNTHESIS OF NATURAL PRODUCT NEPETANUDONE THROUGH THERMALLY FORBIDDEN [4Π+4Π] CYCLOADDITION IN THE PRESENCE OF LIGHT
type
Thesis

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