Syntheses of the fungicide/insecticide allosamidin and a structural isomer
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 3411-3421
- https://doi.org/10.1039/p19940003411
Abstract
A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose. The structural isomer 59 of allosamidin is also reported. Brief biological test results obtained using isomers 1 and 59 are recorded.Keywords
This publication has 37 references indexed in Scilit:
- A general synthetic strategy toward aminocyclopentitol glycosidase inhibitors. Application of palladium catalysis to the synthesis of allosamizoline and mannostatin AJournal of the American Chemical Society, 1993
- Stereocontrolled synthesis of (−)-allosamizoline using D-glucosamine as a chiral templateTetrahedron Letters, 1991
- Total synthesis of allosamidin: an application of the sulfonamidoglycosylation of glycalsJournal of the American Chemical Society, 1991
- Template-directed synthesis of (.+-.)-allosamizoline and its 3,4-epimersJournal of the American Chemical Society, 1990
- Absolute configuration of allosamizoline, an aminocyclitol derivative of the chitinase inhibitor allosamidin.Agricultural and Biological Chemistry, 1988
- Method for the detection and quantitation of chitinase inhibitors in fermentation broths; Isolation and insect life cycle effect of A82516.The Journal of Antibiotics, 1987
- Search for microbial insect growth regulators. II Allosamidin, a novel insect chitinase inhibitor.The Journal of Antibiotics, 1987
- Structures of allosamidins, novel insect chitinase inhibitors, produced by actinomycetes.Agricultural and Biological Chemistry, 1987
- Specific inhibition of Bombyx mori chitinase by allosamidin.Agricultural and Biological Chemistry, 1987
- The structure of allosamidin, a novel insect chitinase inhibitor, produced by Streptomyces Sp.Tetrahedron Letters, 1986