Abstract
In order to establish a simple common methodology for the highly stereoselective and efficient synthesis of macrolide aglycones, 12-membered ring methynolide and 16-membered ring tylonolide were synthesized from D-glucose via the synthesis of respective fragments followed by their coupling (esterification by the Yamaguchi method) and cyclization by the Wittig-Horner reaction under Nicolaou's conditions. This method was extended to the synthesis of 14-membered ring pikronolide and, together with conformational control of macrolide rings, to some typical 16-membered ring aglycones such as carbonolides, leuconolides, maridonolides, etc. A new synthesis of erythronolide A via an extremely efficient macrolactonization by virtue of conformational control and super activation of the seco-acid is also described.
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