A total synthesis of galbonolide B.
An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base mediated macrocyclization of the acetate ester 16 followed by base mediated alkylation and acetal deprotection gave galbonolide B 1.
Parsons
Philip J
PJ
Department of Chemistry, The University of Sussex, Falmer, Brighton, UK. P.J.Parsons@sussex.ac.uk
Pennicott
Lewis
L
Eshelby
James
J
Goessman
Matthias
M
Highton
Adrian
A
Hitchcock
Peter
P
D000080:Acetals / Q000737:chemistry; D000085:Acetates / Q000737:chemistry; D000478:Alkylation; D000935:Antifungal Agents / Q000138:chemical synthesis*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis; D008956:Models, Chemical; D020005:Propanols / Q000737:chemistry
D000080:Acetals; D000085:Acetates; D000935:Antifungal Agents; D007783:Lactones; D020005:Propanols; C047787:neorustmicin A; C006463:allyl alcohol