View stunning SlideShares in full-screen with the new iOS app!Introducing SlideShare for AndroidExplore all your favorite topics in the SlideShare appGet the SlideShare app to Save for Later — even offline
View stunning SlideShares in full-screen with the new Android app!View stunning SlideShares in full-screen with the new iOS app!
PROBLEM SET 3
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.
III. Devise a synthetic route to accomplish the enantioselective synthesis of B from 21,3-one via A.
IV. Provide synthetic routes to accomplish the production of the following compounds given the starting
V. Devise a synthetic routes to accomplish the enantioselective synthesis of the products shown from the
starting materials provided.
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