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Liffert, Raphael; Linden, Anthony; Gademann, Karl (2017). Total synthesis of the sesquiterpenoid periconianone a based on a postulated biogenesis. Journal of the American Chemical Society, 139(45):16096-16099.
The first enantioselective total synthesis of the complex tricarbocyclic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O–H insertion/[3,3]-sigmatropic rearrangement and subsequent α-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Physical Sciences > General Chemistry Life Sciences > Biochemistry Physical Sciences > Colloid and Surface Chemistry |
| Language: | English |
| Date: | 2017 |
| Deposited On: | 18 Jan 2018 17:17 |
| Last Modified: | 17 Apr 2025 01:35 |
| Publisher: | American Chemical Society (ACS) |
| ISSN: | 0002-7863 |
| Additional Information: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.7b10053. |
| OA Status: | Green |
| Publisher DOI: | https://doi.org/10.1021/jacs.7b10053 |
| PubMed ID: | 29076340 |
| Project Information: |
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Liffert, Raphael