Asperidine B : total synthesis and structure correction
A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement wit...
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sg-ntu-dr.10356-1419782023-02-28T19:47:14Z Asperidine B : total synthesis and structure correction Waddell, Lachlan J. N. Watts, Olivia F. B. Saetang, Praphatsorn Rukachaisirikul, Vatcharin Bates, Roderick Wayland School of Physical and Mathematical Sciences Science::Chemistry Piperidine Pyrrolidine A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin. Accepted version 2020-06-12T09:00:18Z 2020-06-12T09:00:18Z 2020 Journal Article Waddell, L. J. N., Watts, O. F. B., Saetang, P., Rukachaisirikul, V., & Bates, R. W. (2020). Asperidine B : total synthesis and structure correction. Tetrahedron Letters, 61(27), 152078-. doi:10.1016/j.tetlet.2020.152078 0040-4039 https://hdl.handle.net/10356/141978 10.1016/j.tetlet.2020.152078 27 61 en Tetrahedron Letters https://doi.org/10.21979/N9/OD7MHF © 2020 Elsevier Ltd. All rights reserved. This paper was published in Tetrahedron Letters and is made available with permission of Elsevier Ltd. application/pdf |
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Science::Chemistry Piperidine Pyrrolidine |
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Science::Chemistry Piperidine Pyrrolidine Waddell, Lachlan J. N. Watts, Olivia F. B. Saetang, Praphatsorn Rukachaisirikul, Vatcharin Bates, Roderick Wayland Asperidine B : total synthesis and structure correction |
| description |
A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Waddell, Lachlan J. N. Watts, Olivia F. B. Saetang, Praphatsorn Rukachaisirikul, Vatcharin Bates, Roderick Wayland |
| format |
Article |
| author |
Waddell, Lachlan J. N. Watts, Olivia F. B. Saetang, Praphatsorn Rukachaisirikul, Vatcharin Bates, Roderick Wayland |
| author_sort |
Waddell, Lachlan J. N. |
| title |
Asperidine B : total synthesis and structure correction |
| title_short |
Asperidine B : total synthesis and structure correction |
| title_full |
Asperidine B : total synthesis and structure correction |
| title_fullStr |
Asperidine B : total synthesis and structure correction |
| title_full_unstemmed |
Asperidine B : total synthesis and structure correction |
| title_sort |
asperidine b : total synthesis and structure correction |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/141978 https://doi.org/10.21979/N9/OD7MHF |
| _version_ |
1759854920200093696 |