Work

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

Year: 2011

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo102327e

Authors: Jacob Y. Cha, G. Leslie Burnett, Yaodong Huang, Jarrod B. Davidson, Thomas R. R. Pettus

Institution: University of California, Santa Barbara

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G6704650334, The Synthesis and Application of Novel Aromatic Materials