Synthesis and Structural Characterization of 1-(-1-Arylpropenon-3-yl)-3,4,6-tri--benzyl-d-glucals and Their Transformation into Pentasubstituted (2,3,4)-Chromanes Pd-Catalyzed Cross Dehydrogenative Coupling Reaction

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2021 May 31

PMID 34056280

Citations 1

Authors

Bhawani Shankar

Vinod Khatri

Banty Kumar

Vipin K Maikhuri

Amit Kumar

Rashmi Tomar

Ashok K Prasad

Affiliations

Soon will be listed here.

Abstract

We have developed an efficient methodology for the synthesis of (2,3,4)-2-hydroxymethyl-3,4-dihydroxy-6-aryl-7-aroylchromanes in which the chirality at the -2, -3, and -4 positions is being drawn from -glucopyranosyl aldehyde, which in turn can be efficiently synthesized from d-glucose. Thus, the synthesis starts with the transformation of sugar aldehyde into 1-(-1-arylpropenon-3-yl)-3,4,6-tri--benzyl-d-glucals using Claisen-Schmidt type condensation reaction with different acetophenones and then to 1,2-disubstituted glucals Pd(II)-catalyzed cross dehydrogenative coupling reaction, which in turn has been efficiently converted into (2,3,4)-chromanes 6π-electrocyclization and dehydrogenative aromatization.

Citing Articles

-Glycopyranosyl aldehydes: emerging chiral synthons in organic synthesis.

Kumar S, Khatri V, Mangla P, Chhatwal R, Parmar V, Prasad A RSC Adv. 2023; 13(29):19898-19954.

PMID: 37404320 PMC: 10316784. DOI: 10.1039/d3ra02122j.

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