New strategy for diene synthesis : application in total synthesis of Palmerolide A
Palladium-catalyzed alkenylation offers one of the most efficient methods for the synthesis of functionalized butadienes. However, due to the need for pre-functionalization of reactants and undesirable formation of stoichiometric amount of waste in the reactions, these processes were rendered neithe...
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| Format: | Thesis |
| Language: | English |
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2013
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| Online Access: | https://hdl.handle.net/10356/51110 |
| _version_ | 1826128132333109248 |
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| author | Wen, Zhenkang |
| author2 | Tang Liangfu |
| author_facet | Tang Liangfu Wen, Zhenkang |
| author_sort | Wen, Zhenkang |
| collection | NTU |
| description | Palladium-catalyzed alkenylation offers one of the most efficient methods for the synthesis of functionalized butadienes. However, due to the need for pre-functionalization of reactants and undesirable formation of stoichiometric amount of waste in the reactions, these processes were rendered neither atom-economical nor environmentally benign. The emphasis of this thesis is focused on the design and development of a palladium-catalyzed cross-coupling reaction of unactivated alkenes with acrylates for the construction of 1,3-diene motifs and its application towards a total synthesis of the natural product, Palmerolide A. In the first introduction chapter, a summary of established methodologies in the construction of 1,3-butadiene system is outlined, ranging from carbonyl olefination to recently emerging olefin metathesis. In particular, the strategy of transition metal-catalyzed alkenylation is thoroughly and intensively discussed. With the increasing demand for more atom- and step-economical methods, we have developed a direct and efficient palladium-catalyzed method for the cross-coupling of homoallylic and allylic alcohols with acrylates that produces dienic alcohols in moderate to high yields, and with good stereoselectivity. |
| first_indexed | 2024-10-01T07:19:56Z |
| format | Thesis |
| id | ntu-10356/51110 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:19:56Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/511102023-02-28T23:53:42Z New strategy for diene synthesis : application in total synthesis of Palmerolide A Wen, Zhenkang Tang Liangfu Loh Teck Peng School of Physical and Mathematical Sciences DRNTU::Science::Chemistry Palladium-catalyzed alkenylation offers one of the most efficient methods for the synthesis of functionalized butadienes. However, due to the need for pre-functionalization of reactants and undesirable formation of stoichiometric amount of waste in the reactions, these processes were rendered neither atom-economical nor environmentally benign. The emphasis of this thesis is focused on the design and development of a palladium-catalyzed cross-coupling reaction of unactivated alkenes with acrylates for the construction of 1,3-diene motifs and its application towards a total synthesis of the natural product, Palmerolide A. In the first introduction chapter, a summary of established methodologies in the construction of 1,3-butadiene system is outlined, ranging from carbonyl olefination to recently emerging olefin metathesis. In particular, the strategy of transition metal-catalyzed alkenylation is thoroughly and intensively discussed. With the increasing demand for more atom- and step-economical methods, we have developed a direct and efficient palladium-catalyzed method for the cross-coupling of homoallylic and allylic alcohols with acrylates that produces dienic alcohols in moderate to high yields, and with good stereoselectivity. DOCTOR OF PHILOSOPHY (SPMS) 2013-01-22T03:03:33Z 2013-01-22T03:03:33Z 2012 2012 Thesis Wen, Z. (2012). New strategy for diene synthesis : application in total synthesis of palmerolide A. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/51110 10.32657/10356/51110 en 118 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry Wen, Zhenkang New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title | New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title_full | New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title_fullStr | New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title_full_unstemmed | New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title_short | New strategy for diene synthesis : application in total synthesis of Palmerolide A |
| title_sort | new strategy for diene synthesis application in total synthesis of palmerolide a |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/51110 |
| work_keys_str_mv | AT wenzhenkang newstrategyfordienesynthesisapplicationintotalsynthesisofpalmerolidea |