Total synthesis of (+)-zaragozic acid C.
A total synthesis of (+)-zaragozic acid C is described. Key features of the synthesis are the use of a double Sharpless asymmetric dihydroxylation reaction of diene 6 to control stereochemistry at four contiguous stereocenters from C3 to C6; the introduction of the C1-side chain by reaction between the anion derived from the dithiane monosulfoxide 27 and the core aldehyde 12; a high yielding, acid-mediated simultaneous acetonide deprotection-dithiane removal-ketalization procedure leading exclusively to the 2, 8-dioxabicyclo[3.2.1]octane core 34; and a novel triple oxidation procedure allowing installation of the tricarboxylic acid.
Armstrong
A
A
School of Chemistry, University of Nottingham, Nottingham NG7 2RD, U. K. A.Armstrong@ic.ac.uk
Barsanti
P A
PA
Jones
L H
LH
Ahmed
G
G
D000924:Anticholesteremic Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D006900:Hydroxylation; D007202:Indicators and Reagents; D013237:Stereoisomerism
D000924:Anticholesteremic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; C079090:zaragozic acid C