Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27607, United States.
Comparative Medicine Institute, North Carolina State University, Raleigh, North Carolina 27695, United States.
Org Lett. 2021 Dec 17;23(24):9559-9562. doi: 10.1021/acs.orglett.1c03782. Epub 2021 Nov 30.
Ansalactam A is an ansa macrolide natural product that contains a densely functionalized spiro-γ-lactam core containing three contiguous stereocenters. This unusual motif distinguishes it from other members of this family and represents a significant synthetic challenge. Herein, we report the development of a stereoselective formal [3+2] cycloaddition reaction for the construction of this key spiro-γ-lactam motif for the first time, thereby enabling access to the northern domain of ansalactam A.
安沙来酰胺 A 是一种含有一个密集功能化的螺-γ-内酰胺核心的安萨大环内酯天然产物,该核心含有三个连续的立体中心。这种不寻常的结构特征使其有别于该家族的其他成员,同时也代表了一个重大的合成挑战。在此,我们首次报道了一种立体选择性的[3+2]环加成反应,用于构建该关键螺-γ-内酰胺结构,从而能够获得安沙来酰胺 A 的北部结构域。