Total synthesis of (−)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline
作者:Byron A. Boon、Yi-Yun Yu、Dale L. Boger
DOI:10.1016/j.tet.2021.132117
日期:2021.5
A concise total synthesis of (−)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4 + 2]/[3 + 2] cycloaddition cascade that formed four C–C bonds, created three new rings, and established five contiguous stereocenters about the new formed
公开了 (-)-4-去乙酰氧基-1-oxovindoline 的简明全合成,在天然产物 4-desacetoxyvindoline 的核心结构中带有单个杂原子交换。合成的核心是强大的恶二唑分子内[4 + 2]/[3 + 2]环加成级联,形成四个C-C键,产生三个新环,并在新形成的中心六元环周围建立五个连续的立体中心。