Title | Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement. |
Publication Type | Journal Article |
Year of Publication | 2018 |
Authors | Li X, Carter RG |
Journal | Org Lett |
Volume | 20 |
Issue | 18 |
Pagination | 5546-5549 |
Date Published | 2018 09 21 |
ISSN | 1523-7052 |
Abstract | The first total syntheses of triptobenzene T, vitexifolin C, 4- epi-triptobenzene L, triptobenzene L, and nepetaefolin F have been accomplished through an enantioselective, common intermediate approach and have enabled the confirmation and/or establishment of the absolute stereochemistry of each natural product synthesized. Application of three new and/or underutilized Pummerer reaction pathways proved critical to the synthetic work. A proline sulfonamide-catalyzed Yamada-Otani reaction was used to access the highly functionalized cyclohexane A ring core, including the C all-carbon quaternary stereocenter. Additionally, the importance of the A ring unsaturation for controlling the stereoselectivity during the C alkylation is showcased. |
DOI | 10.1021/acs.orglett.8b02060 |
Alternate Journal | Org. Lett. |
PubMed ID | 30199260 |