/ E-Alerts

Synthetic study toward tridachiapyrone B

Morgan Cormier, Florian Hernvann and Michaël De Paolis

Beilstein J. Org. Chem. 2022, 18, 1741–1748. https://doi.org/10.3762/bjoc.18.183

Supporting Information

Supporting Information File 1: Experimental details, ¹H and ¹³C spectra of new compounds.
Format: PDF	Size: 3.4 MB	Download

Cite the Following Article

Synthetic study toward tridachiapyrone B

Morgan Cormier, Florian Hernvann and Michaël De Paolis

Beilstein J. Org. Chem. 2022, 18, 1741–1748. https://doi.org/10.3762/bjoc.18.183

How to Cite

Cormier, M.; Hernvann, F.; De Paolis, M. Beilstein J. Org. Chem. 2022, 18, 1741–1748. doi:10.3762/bjoc.18.183

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

File format:

RIS

BibTeX

Include:

Citation for the article above

Citation and complete reference list for the article above

Download

TY  - JOUR
A1  - Cormier, Morgan
A1  - Hernvann, Florian
A1  - De Paolis, Michaël
T1  - Synthetic study toward tridachiapyrone B
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 1741
EP  - 1748
SN  - 1860-5397
DO  - 10.3762/bjoc.18.183
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.183
KW  - α’-methoxy-γ-pyrone
KW  - 2,5-cyclohexadienone
KW  - oxy-Cope
KW  - quaternary carbon
KW  - Robinson-type annulation
N2  - A convergent approach to the skeleton of tridachiapyrone B is described taking advantage of the desymmetrization of α,α’-dimethoxy-γ-pyrone leading to α-crotyl-α’-methoxy-γ-pyrone in one step. To construct the quaternary carbon of the 2,5-cyclohexadienone of the target, a strategy based on the Robinson-type annulation of an aldehyde derived from α-crotyl-α’-methoxy-γ-pyrone was applied. The grafting of the simplified target’s side chain was demonstrated through an oxidative anionic oxy-Cope rearrangement of the tertiary alcohol arising from the 1,2-addition of a 1,3-dimethylallyl reagent to 2,5-cyclohexadienone connected to the α’-methoxy-γ-pyrone motif.
ER  -

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG	Size: 7.4 MB	Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

De Paolis, M. Carbanions of Alkali and Alkaline-Earth Cations: (II) Selectivity of Carbonyl Addition Reactions. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier, 2024. doi:10.1016/b978-0-323-96025-0.00033-8

Explore citations to this article at

Back To Article

Other Beilstein-Institut Open Science Activities

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)