1. Using your knowledge of organic chemistry propose a synthesis of alkyl bromide A starting from the diester shown. Your synthesis should include all reagents required to carry out each transformation. If several steps are required for a given transformation label them as 1) 2) etc. Be sure to indicate the order of addition for reagents if this is important for controlling reaction outcomes (e.g. stereoselectivity or regioselectivity). H3CO O OCH3 Br O A 2. Using your knowledge of organic chemistry propose a synthesis of the natural product C starting from precursors A and B. Your synthesis should include all reagents required to carry out each transformation. If several steps are required for a given transformation label them as 1) 2) etc. Be sure to indicate the order of addition for reagents if this is important for controlling reaction outcomes (e.g. stereoselectivity or regioselectivity). N + O Br O O C A B 3. Draw all possible stereoisomers of the natural product C above and assign configuration to each chiral center. Indicate which might be the most thermodynamically stable and explain your rationale.
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