Deconstruction-reconstruction strategy for accessing valuable polyketides. Preparation of the C15-C24 stereopentad of discodermolide.
An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794, USA. kparker@notes.cc.sunysb.edu
Wang
Peng
P
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009827:Oleandomycin / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D002219:Carbamates; D007783:Lactones; D018942:Macrolides; D011753:Pyrones; D002244:Carbon; C071229:discodermolide; D009827:Oleandomycin