A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues

作者：Cha Jacob Y; Burnett G Leslie; Huang Yaodong; Davidson Jarrod B; Pettus Thomas R R^*

来源：Journal of Organic Chemistry, 2011, 76(5): 1361-1371.

DOI：10.1021/jo102327e

This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,

• 出版日期2011-3-4