dc.contributor.author |
Sidford, Matthew |
en |
dc.date.accessioned |
2007-07-11T23:55:19Z |
en |
dc.date.available |
2007-07-11T23:55:19Z |
en |
dc.date.issued |
2004 |
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dc.identifier.citation |
Thesis (PhD--Chemistry)--University of Auckland, 2004. |
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dc.identifier.uri |
http://hdl.handle.net/2292/917 |
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dc.description.abstract |
An investigation into the synthesis of several analogues of antifungal agents related to the papulacandins was undertaken. Retrosynthetic analysis of these analogues identified phthalide (261) and allylstannane (278) as key intermediates in the synthesis of analogues of type (284).
The key step in the synthesis of phthalide (261) was the ortho formylation via ortholithiation of amide (255). The synthesis of phthalide (261) was carried out over five steps in 35% overall yield from (255).
Synthesis of the allylstannane intermediate from alcohol (351) proved problematic thus preventing further progress in this area of research.
Synthetic studies toward the anti-helicobactericidal phthalides CJ-12,954 (56), CJ-13,014 (57), CJ-13,015 (58), CJ-13,0102 (59), CJ-13,103 (60), CJ-13,104 (61), and CJ-13,108 (62) were undertaken. CJ-12,954 (56) and CJ-13,108 (62) were chosen as initial targets. Retrosynthetic analysis identified phthalide (288), spiroketal ylide (297) and ylide (468) as key intermediates for the synthesis of the natural products (56) and (62). The synthesis of spiroketal epoxide (300) was successfully achieved in fifteen steps starting from materials (386) and (381) in an overall yield of 87o. Unfortunately all attempts to effect ring opening of epoxide (300) were unsuccessful. The racemic synthesis of phthalide (288) was carried out in six steps starting from material 2,4-dimethoxybenzoic acid (296) in 33% overall yield. Wittig coupling of ylide (468) with phthalide (288) allowed complete total synthesis of racemic CJ-13,108 (62) from (288) in 42% overall yield. |
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dc.format |
Scanned from print thesis |
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dc.language.iso |
en |
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dc.publisher |
ResearchSpace@Auckland |
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dc.relation.ispartof |
PhD Thesis - University of Auckland |
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dc.relation.isreferencedby |
UoA1540890 |
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dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
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dc.title |
Synthetic Studies Towards Antibiotics Containing Phthalide Moieties |
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dc.type |
Thesis |
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thesis.degree.discipline |
Chemistry |
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thesis.degree.grantor |
The University of Auckland |
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thesis.degree.level |
Doctoral |
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thesis.degree.name |
PhD |
en |
dc.rights.holder |
Copyright: The author |
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pubs.local.anzsrc |
03 - Chemical Sciences |
en |
pubs.org-id |
Faculty of Science |
en |
dc.identifier.wikidata |
Q112860276 |
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