Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones DOI

Mohammad Sadeq Mousavi,

Antonia Di Mola, Giovanni Pierri

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein we report two processes facilitated by diisopropylethylamine (DIPEA) for the synthesis of novel bridged polycyclic molecule analogues to natural products. The use 4-bromoisochroman-3-one initiated an autoxidation reaction, followed a Diels-Alder cycloaddition in presence electron-deficient dienophiles. Mechanistic studies revealed isochromane-3,4-dione as key intermediate, which undergoes situ dienolization/dearomatization [4 + 2] cycloaddition. Subsequently, and direct application isochromane-3,4-diones reaction enabled development alternative method with enhanced efficiency improved atom economy. In addition chalcones, other enones common electron-poor alkenes, bearing ester, nitro cyano electron-withdrawing groups (including both terminal,

Language: Английский

A systematic and comprehensive review of the properties and synthesis of anticancer heterocyclic natural products DOI Creative Commons

Tirth Chauhan,

Manan Shah

Current Pharmaceutical Analysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Total Synthesis of (±)-Keramaphidin B and (±)-Ingenamine DOI
Erick M. Carreira,

Sebastian Kölbl

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0671 - 0671

Published: June 14, 2024

Key words (±)-keramaphidin B - (±)-ingenamine marine alkaloid Negishi coupling Diels–Alder reaction Appel

Language: Английский

Citations

0
Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones DOI

Mohammad Sadeq Mousavi,

Antonia Di Mola, Giovanni Pierri

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein we report two processes facilitated by diisopropylethylamine (DIPEA) for the synthesis of novel bridged polycyclic molecule analogues to natural products. The use 4-bromoisochroman-3-one initiated an autoxidation reaction, followed a Diels-Alder cycloaddition in presence electron-deficient dienophiles. Mechanistic studies revealed isochromane-3,4-dione as key intermediate, which undergoes situ dienolization/dearomatization [4 + 2] cycloaddition. Subsequently, and direct application isochromane-3,4-diones reaction enabled development alternative method with enhanced efficiency improved atom economy. In addition chalcones, other enones common electron-poor alkenes, bearing ester, nitro cyano electron-withdrawing groups (including both terminal,

Language: Английский

Citations

0