Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement

Citeable URL: https://ir.library.oregonstate.edu/concern/articles/5d86p518k

Descriptions

Attribute Name	Values
Creator	Li, Xin Carter, Rich G.
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-10 all-carbon quaternary stereocenter. Additionally, the importance of the A ring unsaturation for controlling the stereoselectivity during the C-4 alkylation is showcased.
License	Attribution 4.0 (CC BY 4.0)
Resource Type	Article
DOI	https://doi.org/10.1021/acs.orglett.8b02060
Date Issued	2018-09-21
Journal Title	Organic Letters
Journal Volume	20
Rights Statement	In Copyright
Language	English [eng]
ISSN	1523-7060

Thumbnail

Title

Date Uploaded

Visibility

Actions

2018-10-24

Public

Download