Stereoselective synthesis of the lituarine tricyclic spiroacetal.
[reaction: see text] Oxidative cyclizations of 2-(4-hydroxybutyl)furan derivatives provide spirobutenolide acetals directly; on the basis of this methodology, we describe an asymmetric synthesis of a tricyclic spirobutenolide precursor to the C(7-18) fragment common to lituarines A-C.
Robertson
Jeremy
J
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. jeremy.robertson@chem.ox.ac.uk
Meo
Paul
P
Dallimore
Jonathan W P
JW
Doyle
Bryan M
BM
Hoarau
Christophe
C
D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000737:chemistry*
D004852:Epoxy Compounds; D013141:Spiro Compounds; C442895:lituarine A; C442897:lituarine B; C442896:lituarine C