Copper(I)-Mediated 1,2-Metallate Rearrangements of 1-Metallated Glycals

Krzysztof Jarowicki, Philip Kocieński, Zofia Komsta & Anna Wojtasiewicz
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.

2 Related Works

CCDC 676303: Experimental Crystal Structure Determination

K. Jarowicki, P. Kocienski, Z. Komsta & A. Wojtasiewicz
Related Article: K.Jarowicki, P.Kocienski, Z.Komsta, A.Wojtasiewicz|2012|Synthesis|44|946|doi:10.1055/s-0031-1289721

Copper(I)-Mediated 1,2-Metallate Rearrangements of 1-Metallated Glycals

Krzysztof Jarowicki, Philip Kocieński, Zofia Komsta & Anna Wojtasiewicz
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.

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