Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid
To achieve high asymmetric selectivities and high efficiency in biomimetic cationic polyene cyclization is a challenging problem in both academia and industries. The intramolecular acetal-initiated cationic polyene cyclization reaction was first introduced and well developed by W. S. Johnson. Howeve...
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
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2010
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| Online Access: | https://hdl.handle.net/10356/41740 |
| _version_ | 1811691907892379648 |
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| author | Zhao, Yu Jun |
| author2 | Loh Teck Peng |
| author_facet | Loh Teck Peng Zhao, Yu Jun |
| author_sort | Zhao, Yu Jun |
| collection | NTU |
| description | To achieve high asymmetric selectivities and high efficiency in biomimetic cationic polyene cyclization is a challenging problem in both academia and industries. The intramolecular acetal-initiated cationic polyene cyclization reaction was first introduced and well developed by W. S. Johnson. However, there exist some disadvantages in this intramolecular polyene cyclization. The need to incorporate the required acetal into the acyclic precursor added synthetic complexity. In addition, the accommodation of the acetal moiety also diminishes the structural flexibility in the acyclic precursor. These two problems, though minor, could reduce the scope and applicability of the method substantially. The emphasis of this thesis is placed on the evolution of a novel intermolecular acetal-initiated polyene cyclization reaction to overcome these current limitations and manifestation of its applicability on the asymmetric total synthesis of natural products. |
| first_indexed | 2024-10-01T06:27:21Z |
| format | Thesis |
| id | ntu-10356/41740 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:27:21Z |
| publishDate | 2010 |
| record_format | dspace |
| spelling | ntu-10356/417402023-02-28T23:50:27Z Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid Zhao, Yu Jun Loh Teck Peng School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis To achieve high asymmetric selectivities and high efficiency in biomimetic cationic polyene cyclization is a challenging problem in both academia and industries. The intramolecular acetal-initiated cationic polyene cyclization reaction was first introduced and well developed by W. S. Johnson. However, there exist some disadvantages in this intramolecular polyene cyclization. The need to incorporate the required acetal into the acyclic precursor added synthetic complexity. In addition, the accommodation of the acetal moiety also diminishes the structural flexibility in the acyclic precursor. These two problems, though minor, could reduce the scope and applicability of the method substantially. The emphasis of this thesis is placed on the evolution of a novel intermolecular acetal-initiated polyene cyclization reaction to overcome these current limitations and manifestation of its applicability on the asymmetric total synthesis of natural products. DOCTOR OF PHILOSOPHY (SPMS) 2010-08-06T04:08:16Z 2010-08-06T04:08:16Z 2008 2008 Thesis Zhao, Y. J. (2008). Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/41740 10.32657/10356/41740 en 329 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Zhao, Yu Jun Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title | Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title_full | Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title_fullStr | Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title_full_unstemmed | Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title_short | Development of new bio-inspired reactions and application to asymetric total synthesis of antiochic acid |
| title_sort | development of new bio inspired reactions and application to asymetric total synthesis of antiochic acid |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/41740 |
| work_keys_str_mv | AT zhaoyujun developmentofnewbioinspiredreactionsandapplicationtoasymetrictotalsynthesisofantiochicacid |