Formal total synthesis of (-)-saliniketals.
A highly stereoselective formal total synthesis of the ornithine decarboxylase inhibitors (-)-saliniketals A and B is described. The salient features of the synthesis are the utilization of a desymmetrization technique to create six contiguous chiral centers from a single bicyclic precursor as well as substrate-controlled Grignard reaction, intramolecular Wacker-type oxidation, and antialdol reaction following Pirrung-Heathcock conditions.
Yadav
J S
JS
Organic Chemistry Division-I, Indian Institute of Chemical Technology (CSIR), Hyderabad 500007, India. yadavpub@iict.res.in
Hossain
Sk Samad
SS
Madhu
Madasu
M
Mohapatra
Debendra K
DK
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; C517709:saliniketal A; C517708:saliniketal B