Conversion of furans into gamma-hydroxybutenolides: use of sodium chlorite

3,4-disubstituted furans are converted into gamma-hydroxy-butenolides by treatment with NaClO(2) in aqueous EtOH containing NaH(2)PO(4).     

The naturally occurring ketene acetal benesudon: total synthesis and assignment of relative and absolute stereochemistry

The densely functionalized ketene acetal benesudon, which is a bioactive fungal metabolite, was synthesized from D-glucose by a route involving radical cyclization to form the five-membered ring, and oxidative decarboxylation to generate the key central double bond. The originally suggested stereochemistry for the quaternary center C(5) must be revised, as both C(5) epimers were prepared and a comparison with an authentic sample was made. The absolute configuration of benesudon is 4S,5R,6S.     

Oxidative decarboxylation as a route to ketene acetals: assignment of relative and absolute stereochemistry to the fungal metabolite benesudon by total synthesis

The unusual ketene acetal benesudon, which is a bioactive fungal metabolite, was synthesized from d-glucose by a route involving radical cyclization to form the five-membered ring and oxidative decarboxylation to generate the key central double bond. The originally suggested stereochemistry for the quaternary center C(5) must be revised, as both possibilities were prepared and a comparison with an authentic sample was made. The absolute configuration of benesudon is 4S,5R,6S.     

Synthesis of the core structure of the fungal metabolite benesudon: use of oxidative decarboxylation

[chemical reaction: see text]. The core structure (5) of the fungal metabolite benesudon (1) was synthesized, the key step being oxidative decarboxylation of acid 17.