Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 5, Pages 1361-1371Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo102327e
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Funding
- National Institute of General Medical Sciences [GM064831]
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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,
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