Stereoselective total synthesis of (+/-)-pleurospiroketals A and B
| Title | Stereoselective total synthesis of (+/-)-pleurospiroketals A and B |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Thorat, SS, Krishna, GRama, Kontham, R |
| Journal | Journal of Organic Chemistry |
| Volume | 86 |
| Issue | 19 |
| Pagination | 13572-13582 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | A 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. |
| DOI | 10.1021/acs.joc.1c01634 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.354 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry