[formula: see text] A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated SN2' cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/ol0267174 | DOI Listing |
ACS Cent Sci
November 2024
Department of Chemistry, University of California, Berkeley, California 94720, United States.
Angew Chem Int Ed Engl
November 2022
Laboratoire de Synthèse Organique, Ecole Polytechnique, ENSTA, CNRS, Institut Polytechnique de Paris, Route de Saclay, 91128, Palaiseau Cedex, France.
Total syntheses of (+)-cinereain and (-)-janoxepin, two fungal cyclotripeptides featuring a complex heterocyclic core and interesting phytotoxic and antimalarial activities, have been achieved in a convergent manner. A key step in this synthesis is a one-pot cascade initiated by the cyclocondensation of two fragments-a hindered 2-vinylcyclopropane-1-acyl fluoride and an electron-deficient cyclic amidine-to release a reactive spiro[2-vinylcyclopropane-1,5'-pyrimidine-4',6'-dione]. This intermediate underwent a spontaneous retro-Claisen rearrangement that was rationalized by DFT calculations.
View Article and Find Full Text PDFJ Org Chem
July 2022
Department of Chemistry, Graduate School of Science, Kumamoto University, Kurokami 2-39-1, Chûou-Ku, Kumamoto 860-8555, Japan.
The Mn(III)-catalyzed aerobic oxidation of methylenebis(cyclohexane-1,3-dione) enols resulted in 6a-hydroxy-2,3,4,6a,7,8,9,10a-octahydro-1-benzo[]chromene-1,6,10-triones during the formation of 4,5,8,10,11,12-hexahydro-2-benzo[]oxecine-2,6,7,9(3)-tetraones . The mechanism for the formation of was proposed on the basis of the isolation of intermediates , which were transformed into under Claisen and retro-Claisen conditions.
View Article and Find Full Text PDFOrg Biomol Chem
June 2022
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
(±)-Walskiiglucinol A (1a/1b), a pair of rearranged acylphloroglucinol derivatives with a new carbon skeleton, was obtained from . Compounds 1a/1b were the first examples of naturally occurring acylphloroglucinol derivatives possessing a unique 1-oxaspiro[4.4]nonane core bearing a new 5/5 ring system.
View Article and Find Full Text PDFJ Org Chem
May 2022
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
Norprzewalsone A (), a rearranged polyprenylated polycyclic acylphloroglucinol (PPAP) with a new carbon skeleton, along with a new congener, norprzewalsone B (), were isolated from . Compound possessed a new 5/6/5/6/6 pentacyclic ring system based on a spiro[cyclopentane-1,3'-tricyclo[7.4.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!