Synthesis of allahabadolactone A
A synthesis of allahabadolactone A is described employing diastereoselective Diels–Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels–Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed...
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sg-ntu-dr.10356-889522023-02-28T19:31:58Z Synthesis of allahabadolactone A Wang, Kongchen Bates, Roderick Wayland School of Physical and Mathematical Sciences DRNTU::Science::Chemistry Allahabadolactone Hydrogen Peroxide A synthesis of allahabadolactone A is described employing diastereoselective Diels–Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels–Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels–Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent. ASTAR (Agency for Sci., Tech. and Research, S’pore) Accepted version 2019-05-23T05:09:47Z 2019-12-06T17:14:28Z 2019-05-23T05:09:47Z 2019-12-06T17:14:28Z 2017 Journal Article Wang, K., & Bates, R. W. (2017). Synthesis of Allahabadolactone A. The Journal of Organic Chemistry, 82(23), 12624-12630. doi:10.1021/acs.joc.7b02368 0022-3263 https://hdl.handle.net/10356/88952 http://hdl.handle.net/10220/48340 10.1021/acs.joc.7b02368 en The Journal of Organic Chemistry © 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b02368. 15 p. application/pdf |
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DRNTU::Science::Chemistry Allahabadolactone Hydrogen Peroxide |
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DRNTU::Science::Chemistry Allahabadolactone Hydrogen Peroxide Wang, Kongchen Bates, Roderick Wayland Synthesis of allahabadolactone A |
| description |
A synthesis of allahabadolactone A is described employing diastereoselective Diels–Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels–Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels–Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Wang, Kongchen Bates, Roderick Wayland |
| format |
Article |
| author |
Wang, Kongchen Bates, Roderick Wayland |
| author_sort |
Wang, Kongchen |
| title |
Synthesis of allahabadolactone A |
| title_short |
Synthesis of allahabadolactone A |
| title_full |
Synthesis of allahabadolactone A |
| title_fullStr |
Synthesis of allahabadolactone A |
| title_full_unstemmed |
Synthesis of allahabadolactone A |
| title_sort |
synthesis of allahabadolactone a |
| publishDate |
2019 |
| url |
https://hdl.handle.net/10356/88952 http://hdl.handle.net/10220/48340 |
| _version_ |
1759853357691830272 |