Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
A Lewis acid-mediated, 5/6/7/8- reductive hydroalkoxylation cascade on enynols gives expeditious, diastereoselective access to small and medium ring cyclic ethers with a long aliphatic side chain. The brevity of the approach allowed a 4-step, stereoselective total synthesis of (±)-isolaurepan and (±)--lauthisan.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d4cc04461d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Biosynthesis of the tetrahydroxynaphthalene-derived meroterpenoid furaquinocin reductive deamination and intramolecular hydroalkoxylation of an alkene.
Chem Sci
May 2025
Graduate School of Agricultural and Life Sciences, The University of Tokyo 1-1-1 Yayoi, Bunkyo-ku Tokyo 113-8657 Japan
Hybrid isoprenoid-polyketides, known as meroterpenoids, are a family of natural products that exhibit various bioactivities and are promising drug scaffolds. Despite the structural diversity of 1,3,6,8-tetrahydroxynaphthalene (THN)-derived meroterpenoids, such as furaquinocin, naphterpin, and furanonaphthoquinone, several biosynthetic genes for these compounds are conserved, suggesting a shared biosynthetic mechanism. However, the common biosynthetic mechanism and pathway-specific structural diversification mechanisms of these meroterpenoids are not yet fully understood.
View Article and Find Full Text PDFUnlocking a reductive hydroalkoxylation cascade for the stereoselective synthesis of cyclic ethers: total synthesis of (±)-isolaurepan and (±)--lauthisan.
Chem Commun (Camb)
October 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
A Lewis acid-mediated, 5/6/7/8- reductive hydroalkoxylation cascade on enynols gives expeditious, diastereoselective access to small and medium ring cyclic ethers with a long aliphatic side chain. The brevity of the approach allowed a 4-step, stereoselective total synthesis of (±)-isolaurepan and (±)--lauthisan.
View Article and Find Full Text PDFDeciphering substitution effects on reductive hydroalkoxylation of alkynyl aminols for stereoselective synthesis of morpholines and 1,4-oxazepanes: total synthesis of tridemorph and fenpropimorph.
Org Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.
Acid catalysed reductive etherification of -propargyl amino alcohols for the stereoselective synthesis of -2,5/2,6-disubstituted morpholines and -2,6/2,7-disubstituted oxazepanes has been developed. Mechanistic studies revealed that terminal alkynols gave morpholines a 6- hydroalkoxylation-isomerization-reduction cascade. Interestingly, an alkyne hydration-cyclization-reduction sequence is found to be involved in the formation of oxazepanes from alkyl substituted internal alkynols.
View Article and Find Full Text PDFLewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic -Hydroxylamines Gives Stereoselective Access to Isoxazolidines.
Org Lett
April 2023
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Lewis-acid-catalyzed 5 reductive hydroalkoxylation cascade on propargylic -hydroxylamine gave expedient, stereoselective access to isoxazolidine derivatives. The developed method provides a new approach toward the synthesis of isoxazolidine, a biologically privileged scaffold. The synthetic potential of the developed methodology was demonstrated by synthesizing 1,3-aminoalcohol, 4-aminotetrahydropyran, and sedamine natural products.
View Article and Find Full Text PDFVisible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes.
Chem Commun (Camb)
February 2023
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau 79104, Germany.
A visible-light-induced, intramolecular, reductive cyclisation of ketones with an unsaturated hydrocarbon moiety was developed. In contrast to conventional protocols requiring resource precious or hazardous metal sources, this method enables facile access to ketyl radicals under metal-free and mild reaction conditions. By polarity-reversed, ketyl radical hydroalkoxylation of alkynes and allenes, a variety of five-membered (hetero-)cyclic products were generated in good yields with good to excellent stereoselectivities.
View Article and Find Full Text PDF