Studies directed toward the synthesis of hedycoropyrans: total synthesis of des-hydroxy (-)-hedycoropyran B (ent-rhoiptelol B)
| Title | Studies directed toward the synthesis of hedycoropyrans: total synthesis of des-hydroxy (-)-hedycoropyran B (ent-rhoiptelol B) |
| Publication Type | Journal Article |
| Year of Publication | 2022 |
| Authors | Kataria, P, Nomula, R, Kontham, R |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 20 |
| Issue | 2 |
| Pagination | 444-463 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 1477-0520 |
| Abstract | A full account of our efforts directed towards the synthesis of the diarylheptanoid-derived natural products hedycoropyrans that led to the total synthesis of ent-rhoiptelol B is described. In this endeavor, we have attempted two distinct synthetic strategies to access hedycoropyrans A and B, which led us to establish a facile synthetic route for des-hydroxy (-)-hedycoropyran B (ent-rhoiptelol B) from simple and readily accessible building blocks of 4-allylanisole and vanillin, employing Sharpless asymmetric epoxidation, CBS reduction, and an intramolecular AgOTf-catalyzed oxa-Michael reaction of suitably functionalized hydroxy-ynone as key transformations. The investigations disclosed herein will provide insights into designing novel synthetic routes for THP-DAH-derived natural products. |
| DOI | 10.1039/d1ob01972d |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.876 |
Divison category:
Organic Chemistry
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