Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from
Chapter 19, Problem 19.40(choose chapter or problem)
Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from compound A is outlined in the table that follows. Write structural formulas, ignoring stereochemistry, for compounds B through G in this synthesis. (Hint: Zinc, as used in step 4, converts vicinal dibromides to alkenes.) O O Ambrettolide HOC(CH2)5CH O O H3C CH3 O CH(CH2)7CH2OH Compound A Step Reactant Reagents Product 1. Compound A H2O, H+ heat Compound B (C16H32O5) 2. Compound B HBr Compound C (C16H29Br3O2) 3. Compound C Ethanol, H2SO4 Compound D (C18H33Br3O2) 4. Compound D Zinc, ethanol Compound E (C18H33BrO2) 5. Compound E Sodium acetate, acetic acid Compound F (C20H36O4) 6. Compound F KOH, ethanol, then H+ Compound G (C16H30O3) 7. Compound G Heat Ambrettolide (C16H28O2
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