2. The following questions relate to the synthesis of cecropia juvenile hormone (this hormone plays an important role in insect development), which is shown below. MeCOCH,CO,Et, NaH CO,Me Br 2 CO,Et HO- then H+, heat Moo-P OMe RCO3H MeO .CO,Me 5 NaH cecropia juvenile hormone 4 a. Suggest reagents to convert 1 into 2 in two steps. b. Provide a reaction mechanism to explain how 2 is converted into 3. c. Now thinking backwards from the TM (cecropia juvenile hormone), give the structure of compound 5. d. Is the reaction from 5 to the TM regioselective? Explain your answer.
2. The following questions relate to the synthesis of cecropia juvenile hormone (this hormone plays an important role in insect development), which is shown below. MeCOCH,CO,Et, NaH CO,Me Br 2 CO,Et HO- then H+, heat Moo-P OMe RCO3H MeO .CO,Me 5 NaH cecropia juvenile hormone 4 a. Suggest reagents to convert 1 into 2 in two steps. b. Provide a reaction mechanism to explain how 2 is converted into 3. c. Now thinking backwards from the TM (cecropia juvenile hormone), give the structure of compound 5. d. Is the reaction from 5 to the TM regioselective? Explain your answer.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.60P
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