Development of new synthetic methods towards prins cyclization
A brief introduction to major aspects of Prins cyclization is presented in Chapter 1. Two strategies were attempted via exploitation of the steric and electronic effects in Chapter 2, and a novel and efficient trans Prins cyclization reaction was disclosed by exploiting the electronic effect or the...
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| Format: | Theses and Dissertations |
| Language: | English |
| Published: |
2010
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| Online Access: | https://hdl.handle.net/10356/38690 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | A brief introduction to major aspects of Prins cyclization is presented in Chapter 1. Two strategies were attempted via exploitation of the steric and electronic effects in Chapter 2, and a novel and efficient trans Prins cyclization reaction was disclosed by exploiting the electronic effect or the neighboring participation effect. In Chapter 3 & 4, a Friedel-Crafts-Prins cascade reaction was developed to construct polycyclic THP/DHP and furans rings from propargylic and allylic epoxides in an efficient and diastereoselective manner. In Chapter 5, suppression of oxonia-Cope rearrangement was achieved by tuning the reaction conditions and substrates, leading to the development of a novel cis Prins cyclization reaction of allenic alcohols. By far, the application of this methodology to the synthesis of (+)-Sambutoxin was unsuccessful due to the low reactivity of the starting pyridinone aldehyde. |
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