Synthesis of Tri‑<i>O</i>‑acetyl‑d‑allal from Levoglucosenone

Tri-<i>O</i>-acetyl-d-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2-thione ring

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with a Cellulose-Derived Chiral Enone. A Novel Route for Organocatalysts Development

Cellulose-derived chiral pyrrolidines were synthesized in excellent yields, regioselectivities, and stereoselectivities via a 1,3-dipolar cycloaddition reaction between levoglucosenone and azomethine ylides. An unprecedented isomerization event led to a new family of pyrrolidines with an unusual relative stereochemistry. Preliminary results showed that these compounds are promising organocatalysts for iminium ion-based asymmetric Diels–Alder reactions

Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through <i>retro</i>-aza-Michael//aza-Michael Isomerizations

The design and synthesis of biomass-derived triazoles and the <i>in vitro</i> evaluation as potential anticancer agents are described. The discovery of base-catalyzed <i>retro</i>-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues

Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through <i>retro</i>-aza-Michael//aza-Michael Isomerizations

The design and synthesis of biomass-derived triazoles and the <i>in vitro</i> evaluation as potential anticancer agents are described. The discovery of base-catalyzed <i>retro</i>-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues

Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through <i>retro</i>-aza-Michael//aza-Michael Isomerizations

The design and synthesis of biomass-derived triazoles and the <i>in vitro</i> evaluation as potential anticancer agents are described. The discovery of base-catalyzed <i>retro</i>-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues

Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through <i>retro</i>-aza-Michael//aza-Michael Isomerizations

The design and synthesis of biomass-derived triazoles and the <i>in vitro</i> evaluation as potential anticancer agents are described. The discovery of base-catalyzed <i>retro</i>-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues