Griseolic acid

Griseolic Acids. The three griseoHc acids. A, B, and C (46—48), have been isolated from S. griseoaurantiacus (1,142). They are potent inhibitors of... 

Tulshian, D, Doll, R J, Stansberry, MF, McPhail, A T, Total synthesis of griseolic acid derivatives from D-glucose, J. Org. Chem., 56, 6819-6822, 1991. 

Vinyl halide is a useful synthetic intermediate for natural products. Knapp et al. reported the synthesis of griseolic acid B (130) via intramolecular radical cychzation of vinyl iodide [40]. Aldehyde 125 was reacted with hydrazine to give hydrazone 126, which was further... 

Another way in which 2,5-dihydrofurans could be made was by an intramolecular radical cyclization of a vinyl iodide with an a,p-unsaturated ester as depicted below. Griseolic acid B was synthesized utilizing this cyclization as the key step <01OL3583>. 

T-Deoxy Griseolic acid B. 7 -Desoxygri-seolic acid [98890-01-8]... 

CmHisNjO, 365.302 From Streptomyces griseoaurantiacus. Inhibits various cyclic nucelotide phosphodiesterases Less toxic than Griseolic acid. Cryst. +2H2O. Sol. H2O. 

The C(4 )-C(5 )-dihydro cis-analogue (20) of griseolic acid has been prepared, and found to be a much weaker inhibitor of phosphodiesterase activity than the parent acid or the C(4 ) trans-fused... 

Further work on griseolic acid analogues has been reported (see Vol. 25, p. 232), giving guanosine analogues, e.g. 28, instead of adenine derivatives and its 3, 4 -stereoisomers together with carbocyclic analogues. Other carbocyclic nucleoside derivatives of aristeromycin and a synthesis of carbovir are mentioned in Chapter 20, and a synthesis of the carbocyclic nucleoside precursor, Ohno s lactone, is referred to in Cluster 18. 

---