Problem: Propose a sequence of reactions which will convert the indicated starting material into the desired target compound. In addition to the starting material, you may use any reaction conditions listed in the “menu” provided below. For each reaction in your synthesis, write a letter from the menu in the small box above the reaction arrow to indicate the reaction conditions used, and write the structure that is formed in the large box on the products side of the reaction arrow. If the product of a reaction is a racemic mixture, it is only necessary to draw one enantiomer. Be sure to show stereochemistry clearly and unambiguously where necessary! All of the boxes should end up filled with a letter or a structure if your answer is correct – additional steps should not be necessary!

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Problem Details

Propose a sequence of reactions which will convert the indicated starting material into the desired target compound. In addition to the starting material, you may use any reaction conditions listed in the “menu” provided below. For each reaction in your synthesis, write a letter from the menu in the small box above the reaction arrow to indicate the reaction conditions used, and write the structure that is formed in the large box on the products side of the reaction arrow. If the product of a reaction is a racemic mixture, it is only necessary to draw one enantiomer. Be sure to show stereochemistry clearly and unambiguously where necessary! All of the boxes should end up filled with a letter or a structure if your answer is correct – additional steps should not be necessary!

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Addition Retrosynthesis concept. If you need more Addition Retrosynthesis practice, you can also practice Addition Retrosynthesis practice problems.

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Based on our data, we think this problem is relevant for Professor Hoeger's class at UCSD.