Abstract
1,2-Metallate rearrangements involving reaction of 1-metallated
glycals with organolithium reagents under copper(I) mediation give
alkenylpolyol chains in 45-91% yield (19 examples). The
reaction was applied to a formal synthesis of KRN7000 as well as
a synthesis of a Δ5,6 -ceramide derivative.
Key words
1,2-metallate rearrangement - retro-[1,4]-Brook
rearrangement - 1-metallated glycals - cuprates - organolithiums - KRN7000
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