skeletal rearrangement
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Reactions ◽  
2022 ◽  
Vol 3 (1) ◽  
pp. 70-86
Author(s):  
Yassir Al-Jawaheri ◽  
Marc Colin Kimber

1,3-Dienes are vital building blocks in organic synthesis. They underpin many fundamental synthetic transformations and are present in numerous natural products and drug candidate molecules. The rearrangement of an alkylallene to a 1,3-diene is an atom efficient, redox neutral, transformation that provides a straightforward synthetic route to functionalized 1,3-dienes. Herein, we provide an account of this transformation using allenes that are not predisposed by the presence of heteroatoms or electron-withdrawing groups directly attached to the allene. Early reports of this skeletal rearrangement are acid-mediated approaches, with limited substrate scope, but they provide valuable mechanistic insights. More recent transition metal-mediated approaches that exhibit improved substrate scope are described, together with isolated examples that have utilized this rearrangement.


Oncogene ◽  
2021 ◽  
Author(s):  
Ze Zhang ◽  
Ruoyan Liu ◽  
Yafei Wang ◽  
Yun Wang ◽  
Yanjie Shuai ◽  
...  

Author(s):  
Alexey V. Zakharov ◽  
Anton V. Yadykov ◽  
Elena B. Gaeva ◽  
Anatoly V. Metelitsa ◽  
Valerii Z. Shirinian

2021 ◽  
Author(s):  
Hui Ming Ge ◽  
Fang Wen Jiao ◽  
Yi Shuang Wang ◽  
Xue Ting You ◽  
Wanqing Wei ◽  
...  

Author(s):  
Hui Ming Ge ◽  
Fang Wen Jiao ◽  
Yi Shuang Wang ◽  
Xue Ting You ◽  
Wanqing Wei ◽  
...  

Organics ◽  
2021 ◽  
Vol 2 (3) ◽  
pp. 306-312
Author(s):  
Takahiro Suzuki ◽  
Riko Nagahama ◽  
Muhammad Aiman Fariz ◽  
Yuki Yukutake ◽  
Kazutada Ikeuchi ◽  
...  

Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.


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