Explorations of Stemona Alkaloid-Inspired Analogues: Skeletal Modification and Functional Group Diversification

摘要

A tandem Diels-Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles such as indoles and quinolines or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold generation sequence and the diversification steps could be manipulated to provide regio- and diastereochemically-pure products.