Total synthesis of angelone enabled by a remarkable biomimetic sequence
The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation–elimination, 6π-electrocyclization, visible light-promoted singlet O2 Diels–Alder reaction, Kornblum–DeLaMare-type peroxide rearrangement, 6π-electrocyclic ring-openin...
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| Veröffentlicht in: | Tetrahedron 2012-05, Vol.68 (21), p.3952-3955 |
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| container_issue | 21 |
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| container_title | Tetrahedron |
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| creator | Tan, Haibo Chen, Xinzheng Liu, Zheng Wang, David Zhigang |
| description | The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation–elimination, 6π-electrocyclization, visible light-promoted singlet O2 Diels–Alder reaction, Kornblum–DeLaMare-type peroxide rearrangement, 6π-electrocyclic ring-opening, and conjugative addition–elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities.
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| doi_str_mv | 10.1016/j.tet.2012.03.076 |
| format | Article |
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| ispartof | Tetrahedron, 2012-05, Vol.68 (21), p.3952-3955 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Access via ScienceDirect (Elsevier) |
| subjects | Biomimetic synthesis Biomimetics Diels-Alder reactions Diels–Alder Reaction Electrocyclization Journeys Kornblum–DeLaMare Rearrangement Peroxides Singlet oxygen Stands Strategy Synthesis Tetrahedrons |
| title | Total synthesis of angelone enabled by a remarkable biomimetic sequence |
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