Total synthesis of angelone enabled by a remarkable biomimetic sequence

详细信息	查看全文 | 推荐本文 |

• 作者：Haibo Tan ; Xinzheng Chen ; Zheng Liu ; David Zhigang Wang ; ^{dzw@pkusz.edu.cn} ; ^{dzw@szpku.edu.cn}
• 关键词：Singlet oxygen ; Diels&ndash ; Alder Reaction ; Electrocyclization ; Kornblum&ndash ; DeLaMare Rearrangement ; Biomimetic synthesis
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：27 May, 2012
• 卷：68
• 期：21
• 页码：3952-3955
• 文件大小：604 K

摘要

The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation-elimination, 6蟺-electrocyclization, visible light-promoted singlet O₂ Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6蟺-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.