TitleTotal Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement.
Publication TypeJournal Article
Year of Publication2018
AuthorsLi X, Carter RG
JournalOrg Lett
Date Published2018 09 21

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.

Alternate JournalOrg. Lett.
PubMed ID30199260