Tuning of alpha-silyl carbocation reactivity into enone transposition: application to the synthesis of peribysin D, E-volkendousin, and E-guggulsterone
| Title | Tuning of alpha-silyl carbocation reactivity into enone transposition: application to the synthesis of peribysin D, E-volkendousin, and E-guggulsterone |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Athawale, PR, Zade, VM, Krishna, GRama, D. Reddy, S |
| Journal | Organic Letters |
| Volume | 23 |
| Issue | 17 |
| Pagination | 6642-6647 |
| Date Published | SEP |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence. |
| DOI | 10.1021/acs.orglett.1c02173 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.005 |
Divison category:
Organic Chemistry
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