Synthetic studies toward anisatin: a formal synthesis of (+/-)-8-deoxyanisatin.
[figure: see text] An efficient strategy to construct the congested C-7a quaternary chiral center of anisatin was developed, by way of an Eschenmoser-Claisen rearrangement. Conversion of the resultant amide to Kende's epsilon-lactone intermediate 3 in four steps completed a concise formal synthesis of (+/-)-8-deoxyanisatin (2).
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Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543. chmlohtp@nus.edu.sg
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D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D007783:Lactones; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010947:Plants, Toxic; D012639:Seeds; D012717:Sesquiterpenes; D013141:Spiro Compounds / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D007783:Lactones; D012717:Sesquiterpenes; D013141:Spiro Compounds; C031244:anisatin