Problem set 3 answer key

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  • 1. CHEMISTRY 534 I. PROBLEM SET 3 FALL 2013 DUE MON. OCT. 14, 2013 These assigned problems are for drill only. They will not be graded. a. Do Carey and Sundberg, Part B; Ch. 2: 1a, c, e, g, j; 2e, h, i, j, n, u; 3b, d, f, h, j; 4b, c, f, g, i; 9; 12; 15a, d, e; 17. 5th Ed.:1a, c, e, g, j; 2e, h, i, j, n, u; 3b, d, f, h, j; 4b, c, f, g, i; 9; 12a, b; 14a, d, e. b. Do Carey and Sundberg, Part B; Ch. 2: 2b, k, p, r, s; 3a, f, 4b, e; 6b; 7a, 14b. 5th Ed.: 2b, k, p, r, s; 3a, f, 4b, e; 6b; 7a II. Devise syntheses of the following compounds in diastereo- and enantioenriched form using readily available starting materials. a. b. c.
  • 2. d. e. f. h. (There’s no g) i.
  • 3. j. k. l. m.
  • 4. III. Devise a synthetic route to accomplish the enantioselective synthesis of B from 21,3-one via A. methylcyclohexane- IV. Provide synthetic routes to accomplish the production of the following compounds given the starting materials provided. a. b. c.
  • 5. V. Devise a synthetic routes to accomplish the enantioselective synthesis of the products shown from the starting materials provided. a. b. c.
  • 6. VI. The total synthesis of rutamycin B represents a tour-de-force illustration of the power of asymmetric aldol reactions. Read the account of this synthesis (J. Am. Chem. Soc. 1993, 115, 11446) and identify the key aldol disconnections by drawing those subunits on the full structure. For one syn aldol and one anti aldol disconnection, provide the actual substrates used and provide a transition structure rationale for the stereochemical outcome.