Synthesis of the tetrahydropyran fragment of bistramide D
A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone buil...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2014
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| Online Access: | https://hdl.handle.net/10356/101581 http://hdl.handle.net/10220/24157 |
| _version_ | 1811680292625186816 |
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| author | Bates, Roderick Wayland Li, Lu Palani, Kalpana Phetsang, Wanida Loh, Joanna Kejun |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Bates, Roderick Wayland Li, Lu Palani, Kalpana Phetsang, Wanida Loh, Joanna Kejun |
| author_sort | Bates, Roderick Wayland |
| collection | NTU |
| description | A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions. |
| first_indexed | 2024-10-01T03:22:44Z |
| format | Journal Article |
| id | ntu-10356/101581 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:22:44Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1015812020-06-05T06:29:09Z Synthesis of the tetrahydropyran fragment of bistramide D Bates, Roderick Wayland Li, Lu Palani, Kalpana Phetsang, Wanida Loh, Joanna Kejun School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Bistramide D Metathesis A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions. MOE (Min. of Education, S’pore) 2014-10-30T03:04:39Z 2019-12-06T20:40:51Z 2014-10-30T03:04:39Z 2019-12-06T20:40:51Z 2014 2014 Journal Article Bates, R. W., Li, L., Palani, K., Phetsang, W., & Loh, J. K. (2014). Synthesis of the tetrahydropyran fragment of bistramide D. Asian journal of organic chemistry, 3(7), 792-796. 2193-5807 https://hdl.handle.net/10356/101581 http://hdl.handle.net/10220/24157 10.1002/ajoc.201402052 en Asian journal of organic chemistry Asian journal of organic chemistry © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| spellingShingle | Science::Chemistry::Organic chemistry Bistramide D Metathesis Bates, Roderick Wayland Li, Lu Palani, Kalpana Phetsang, Wanida Loh, Joanna Kejun Synthesis of the tetrahydropyran fragment of bistramide D |
| title | Synthesis of the tetrahydropyran fragment of bistramide D |
| title_full | Synthesis of the tetrahydropyran fragment of bistramide D |
| title_fullStr | Synthesis of the tetrahydropyran fragment of bistramide D |
| title_full_unstemmed | Synthesis of the tetrahydropyran fragment of bistramide D |
| title_short | Synthesis of the tetrahydropyran fragment of bistramide D |
| title_sort | synthesis of the tetrahydropyran fragment of bistramide d |
| topic | Science::Chemistry::Organic chemistry Bistramide D Metathesis |
| url | https://hdl.handle.net/10356/101581 http://hdl.handle.net/10220/24157 |
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