Stereoselective total synthesis of (+/-)-pleurospiroketals A and B

TitleStereoselective total synthesis of (+/-)-pleurospiroketals A and B
Publication TypeJournal Article
Year of Publication2021
AuthorsThorat, SS, Krishna, GRama, Kontham, R
JournalJournal of Organic Chemistry
Volume86
Issue19
Pagination13572-13582
Date PublishedOCT
Type of ArticleArticle
ISSN0022-3263
AbstractA full account of our efforts toward the stereoselective total synthesis of sesquiterpenoid-derived natural products (+/-)-pleurospiroketals A and B is described. Commercially available 3-methyl-2-cyclohexenone and 2,2-dimethyloxirane were used as key building blocks, and the substrate-controlled stereoselection was exploited to access the entire stereochemistry of these natural products. Initially, a planned synthetic route involving a [6,5]-bicyclic lactone intermediate was found to be insurmountable, and the later strategy comprising OsO4-NMO-mediated dihydroxylation of 3-methyl-2-cyclohexenone, followed by Luche reduction, Eschenmoser methylenation, and Bronsted acid-induced spiroketalization steps, was ultimately identified as the reliable strategy.
DOI10.1021/acs.joc.1c01634
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.354
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry

Add new comment