A concise synthesis of the tetracyclic skeleton of palhinine alkaloids is described. The approach features a bifunctional Lewis acid promoted Diels-Alder/carbocyclization cascade for the rapid construction of the isotwistane (tricyclo[4.3.1.03,7]decane) core. This key reaction is highly diastereoselective and could be carried out on gram scale. The cyclization product already possesses the completed ring system of palhinine alkaloids and could potentially be further functionalized to palhinine A.
|Number of pages||4|
|Journal||Organic Chemistry Frontiers|
|Early online date||8 Jul 2020|
|Publication status||Published - 21 Aug 2020|
Scopus Subject Areas
- Organic Chemistry