Synthetic studies towards halichondramides, and related novel tris-oxazole containing macrolides from marine organisms. A concise route to the keto-triol formyl …
MJ Kiefel, J Maddock, G Pattenden - Tetrahedron letters, 1992 - Elsevier
A synthesis of the keto-triol formyl enamine moiety (3) in the marine metabolite
halichondramide (1) is described. The synthesis features judicious applications of the Evans
chiral aldol protocol in combination with the controlled ring opening of chiral α-epoxy alcohol
precursor molecules to elaborate the units (5) and (6). A Wadsworth-Emmons coupling
between (5) and (6) next provided (18), which was then elaborated to (3) via the key
intermediates (19) and (21).
halichondramide (1) is described. The synthesis features judicious applications of the Evans
chiral aldol protocol in combination with the controlled ring opening of chiral α-epoxy alcohol
precursor molecules to elaborate the units (5) and (6). A Wadsworth-Emmons coupling
between (5) and (6) next provided (18), which was then elaborated to (3) via the key
intermediates (19) and (21).
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