Synthesis of the Briarane northern hemisphere
207 p.
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2011
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| Online Access: | https://hdl.handle.net/10356/47499 |
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sg-ntu-dr.10356-474992023-02-28T23:43:31Z Synthesis of the Briarane northern hemisphere Attapol Pinsa Roderick Wayland Bates School of Physical and Mathematical Sciences DRNTU::Engineering::Computer science and engineering 207 p. A large group of marine natural products isolated over the last few years is the briaranes. Over 300 have been isolated, all based on a ring system containing a six membered ring, a ten membered ring and a butenolide, or its oxidised form. Biological studies on the briaranes have revealed a range of activities. Our approach to the synthesis of the briaranes uses a modular approach that should be sufficiently flexible to allow for the synthesis of a variety of these natural products. The preparation of the six-membered ring containing with upper chain as a potential building block was achieved. The Robinson annulation reaction employing P-ketoesters under very mild conditions could not be used to prepare the desired cyclohexenone ester. However, the six-membered ring was obtained by an unusual Diels-Alder reaction of a sulfonyl diene. The Diels-Alder adduct was further manipulated by a series of reactions including oxidative desulfonylation, Eschenmoser-Claisen rearrangement, halo-lactonisation, and enolate hydroxylation using MoOPD. DOCTOR OF PHILOSOPHY (SPMS) 2011-12-27T08:30:25Z 2011-12-27T08:30:25Z 2010 2010 Thesis Attapol Pinsa. (2010). Synthesis of the Briarane northern hemisphere. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/47499 10.32657/10356/47499 Nanyang Technological University application/pdf |
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NTU Library |
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Asia |
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Singapore Singapore |
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DRNTU::Engineering::Computer science and engineering |
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DRNTU::Engineering::Computer science and engineering Attapol Pinsa Synthesis of the Briarane northern hemisphere |
| description |
207 p. |
| author2 |
Roderick Wayland Bates |
| author_facet |
Roderick Wayland Bates Attapol Pinsa |
| format |
Theses and Dissertations |
| author |
Attapol Pinsa |
| author_sort |
Attapol Pinsa |
| title |
Synthesis of the Briarane northern hemisphere |
| title_short |
Synthesis of the Briarane northern hemisphere |
| title_full |
Synthesis of the Briarane northern hemisphere |
| title_fullStr |
Synthesis of the Briarane northern hemisphere |
| title_full_unstemmed |
Synthesis of the Briarane northern hemisphere |
| title_sort |
synthesis of the briarane northern hemisphere |
| publishDate |
2011 |
| url |
https://hdl.handle.net/10356/47499 |
| _version_ |
1759855255850319872 |