An Improved Synthesis of Cyclic Hydroxamic Acids from Gramineae
- 1 March 1998
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 28 (5) , 903-912
- https://doi.org/10.1080/00032719808006490
Abstract
The boron trichloride sensitive methoxymethyl (MOM) protecting group has been used to efficiently synthesize polymethoxylated derivatives of the benzoxazinone family of cyclic hydroxamic acids. The MOM group allows the unveiling of the hemiacetal at C-2 of these compounds without demethylating ring methoxy substituents, resulting in greatly increased yields.Keywords
This publication has 24 references indexed in Scilit:
- Cathepsin B in osteoarthritis: zonal variation of enzyme activity in human femoral head cartilage.Annals of the Rheumatic Diseases, 1995
- Cysteine Proteinase Inhibitors Decrease Articular Cartilage and Bone Destruction in Chronic Inflammatory ArthritisArthritis & Rheumatism, 1994
- Synthesis and Reactivity of Cyclic Hydroxamic AcidsPublished by American Chemical Society (ACS) ,1992
- Nature of papain products resulting from inactivation by a peptidyl O‐acyl hydroxamateFEBS Letters, 1991
- Competing redox and inactivation processes in the inhibition of cysteine proteinases by peptidyl O-acylhydroxamates. Carbon-13 and nitrogen-15 NMR evidence for a novel sulfenamide enzyme adductJournal of the American Chemical Society, 1991
- Analogs of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA): decomposition to benzoxazolinones and reaction with .beta.-mercaptoethanolThe Journal of Organic Chemistry, 1991
- Reaction of dimboa, a resistance factor from cereals, with α-chymotrypsinPhytochemistry, 1990
- Peptidyl O-acyl hydroxamates: Potent new inactivators of cathepsin BBiochemical and Biophysical Research Communications, 1988
- Benzoxazinones from Coix lachryma-jobi var. ma-yuenPhytochemistry, 1985
- Reaction of a cyclic hydroxamic acid from gramineae with thiolsPhytochemistry, 1982