Question

Help with synthesis of an antibiotic macrolide.

Macrolides are large ring lactones (cyclic esters) which have been shown to have both anti-tumor and antibiotic activity. In the synthesis of an antibiotic macrolide, Compound A(C_8H_16O_3) was prepared. A was transformed into B(C_8H_14O_3) using pyridinium chlorochromate (PCC) in methylene chloride. B reacts with one equivalent of vinyl Grignard reagent to yield C(C_10H_18O_3) after workup in acidic water. If excess vinyl Grignard is used, F (shown below) is formed. C, when placed in a strongly basic solution of KOH, forms the salt K^+ C_8H_13O_3^-, D, which can be reacted with one equivalent of acetic anhydride (CH_3CO)_2O, then treated with acidic water to form compound E, shown below. Identify A, B, C and D.

Answer 1

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