SummaryThis is a review of our efforts toward the synthesis of a group of natural products that display noteworthy biological activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits.
The paper reviews the oxidation of oximes to nitrile oxides with hypervalent iodine reagents, especially PhI(OAc) 2 , and the synthetic uses of such a transformation. Side reactions attending the process are also discussed.
The Ti(IV)-catalyzed Ugi condensation of α-amino acids with electron-rich aromatic aldehydes performs adequately even with sterically demanding α-amino carboxylate salts. The reaction occurs diastereoselectively, in some cases with virtually complete diastereoselectivity. A stereochemical rationale for the reaction is proposed.
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