Total synthesis of (-)-saliniketals A and B.
A stereocontrolled total synthesis of the orthinine decarboxylase inhibitors saliniketals A and B is described. Key features of the 17-step route include the use of two boron aldol/reduction sequences to control six of the nine stereocenters, an intramolecular Wacker-type cyclization to install the bicyclic acetal core, and a late-stage Stille coupling to append the requisite (2 Z,4 E)-dienamide.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk
Razzak
Mina
M
Anderson
Edward A
EA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D008848:Micromonosporaceae / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; C517709:saliniketal A; C517708:saliniketal B