The following stereospecific synthesis is part of the scheme used by E. J. Corey of

Chapter 21, Problem 21.55

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The following stereospecific synthesis is part of the scheme used by E. J. Corey of Har-vard University in the synthesis of erythronolide B, the precursor of the erythromycinantibiotics. In this remarkably simple set of reactions, the relative configurations of fivechiral centers are established. (a) Propose a mechanism for the conversion of 2,4,6-trimethylphenol to compound A.(b) Account for the stereoselectivity and regioselectivity of the three steps in the con-version of compound C to compound F.(c) Is compound F produced in this synthesis as a single enantiomer or as a racemicmixture? Explain.

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