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MT1_Wi06 - NU Winter 2006 MT1 Chem 210-2 1 1(20 pts For a...

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NU, Winter 2006 MT1 Chem 210-2 1 1. (20 pts) For a, gives the IUPAC name of the structure shown, be mindful of the stereochemical designation. For b-e, complete the following reactions, be careful to give all the major carbon- containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) OMe b) OH 1) PBr 3 2) KO t Bu, heat 3) Hi heat: 160 o C Hint: 3 rd step will happen. c) 1) NBS, h ν 2) KO t Bu, heat 3) 1 equiv mCPBA 4) TsOH, MeOH 5) Swern’s reagent O OMe d) + Br 1) Heat 2) O 3 3) Me 2 S e) + O MeO O OMe Hi heat: 160 o C
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NU, Winter 2006 MT1 Chem 210-2 2 2. (20 pts) Propose a curved arrow mechanism for the following reactions, showing every proton– transfer steps. a) O O O HO O H 3 O + , H 2 O Hint: This is the deprotection of the 2-pyranyl protecting group b) S O O 140 o C S O O + Hint: This is similar to a retro-Diels-Alder
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NU, Winter 2006 MT1 Chem 210-2 3 3) (20 pts) Consider the following equilibrium O O more stable less stable a)
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