Synthesis 2012(6): 946-952  
DOI: 10.1055/s-0031-1289721
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Krzysztof Jarowicki, Philip Kocieński*, Zofia Komsta, Anna WojtasiewiczInstitute of Process Research & Development, School of Chemistry, Leeds University, Leeds LS2 9JT, UK
e-Mail: p.j.kocienski@leeds.ac.uk;
Further Information

Publication History

Received 2 December 2011
Publication Date:
24 February 2012 (eFirst)

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.