MANGANESE-MEDIATED ALLYL ADDITION TO ENOLIZABLE ALDEHYDE AND KETONES. AN APPROACH FOR INTRODUCTION OF ACETONYL SIDE CHAIN AT C(9) OF ANTHRACYCLINE ANTIBIOTICS

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Abstract
Allyl addition to enolizable aldehyde and ketones is achieved efficiently with manganese reagents generated by the reaction of allyl bromide with MnCl2–LiAlH4 or Mn powder. The Wacker oxidation of the β-tetralone adducts gives an acetonyl moiety typical to an anti-tumor antibiotic, feudomycin.