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Synthesis and antimicrobial screening of some quinonoid systems
Author(s)
Hugo, Victor Ignatius
Date Issued
1996
Type
Thesis
Publisher
Cape Technikon
Abstract
A new general synthetic strategy for the synthesis of benzo[c]pyranquinones,
with a view to making the route more generally applicable to the synthesis of
naturally occurring naphtho[2,3-c]pyranquinones of potential importance as
antimicrobial agents, has been developed. This synthetic approach afforded,
inter alia, the natural products, is oeleutherin and hongconin (as their
racemates) in good overall yield.
A new high-yielding synthetic route for the synthesis of 1,5-dimethoxy-4naphthol,
2-allyl-5-methoxy-I,4-naphthoquinone and 3-acetyl-5-methoxy-I,4naphthoquinone,
all ofwhich are key intermediates in several laboratory routes
to naturally occurring naphtho[2,3-c]pyranquinones, has also been developed.
A key-step in their formation is respective methylation, allylation or
acetylation of a common intermediate Diels-Alder adduct.
A feasible route to a naphtho[2,3-c]pyranone was developed. This model
route is envisaged to be generally applicable for the synthesis of higher
oxygenated naphtho[2,3-c]pyranones by virtue ofthe nature of the conditions
and reagents used in this synthetic route.
The target quinones and some of their precursors were evaluated for
antimicrobial activity and specificity in vitro. This showed that the
benzo[c]pyranquinones have a broader specificity spectrum than their
naphtho[2,3-c] or naphtho[2,3-b] analogues.
with a view to making the route more generally applicable to the synthesis of
naturally occurring naphtho[2,3-c]pyranquinones of potential importance as
antimicrobial agents, has been developed. This synthetic approach afforded,
inter alia, the natural products, is oeleutherin and hongconin (as their
racemates) in good overall yield.
A new high-yielding synthetic route for the synthesis of 1,5-dimethoxy-4naphthol,
2-allyl-5-methoxy-I,4-naphthoquinone and 3-acetyl-5-methoxy-I,4naphthoquinone,
all ofwhich are key intermediates in several laboratory routes
to naturally occurring naphtho[2,3-c]pyranquinones, has also been developed.
A key-step in their formation is respective methylation, allylation or
acetylation of a common intermediate Diels-Alder adduct.
A feasible route to a naphtho[2,3-c]pyranone was developed. This model
route is envisaged to be generally applicable for the synthesis of higher
oxygenated naphtho[2,3-c]pyranones by virtue ofthe nature of the conditions
and reagents used in this synthetic route.
The target quinones and some of their precursors were evaluated for
antimicrobial activity and specificity in vitro. This showed that the
benzo[c]pyranquinones have a broader specificity spectrum than their
naphtho[2,3-c] or naphtho[2,3-b] analogues.
Additional information
Thesis (DTech(Chemistry)) --- Cape Technikon, Cape Town, 1996
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