Titanium(IV)-Promoted
Regioselective Nucleophilic
Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as
a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application
to Stereoselective Total Synthesis of Macrolides
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Abstract
Titanium(IV)-promoted regioselective ring-opening reaction
of <i>chiral epoxy–allyl alcohols</i> (Sharpless
conditions
as the key strategic step) is developed as a tool for ready access
to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic
utility of products thereof was demonstrated through the RCM based
stereoselective synthesis of various natural products