2,3-Dihydroxy-4-butyrolactone

Oxidation of this product by potassium permanganate affords 2,3-dihydroxy-4-butyrolactone. ... 

Dihydroxy-4-butyrolactone, 45, 24 Diisopropylcarbodiimide, 46, 98 Diketene, pyrolysis to ketene, 46, SO -Dimethylaminobenzaldehyde, conversion to 3,g-dichloro- -dimethyl-aminostyrene, 46, 34... 

Dihydroxy-4-butyrolactone, 46, 24 Diimide, in reduction of double bonds,... 

The original preparation of y-crotonolactone by Lespieau involved a five-step sequence from epichlorohydrin and sodium cyanide. A recent detailed study of this procedure reported an overall yield of 25% for the lactone. Glattfeld used a shorter route from glycerol chlorohydrin and sodium cyanide hydrolysis and distillation of the intermediate dihydroxy acid yielded y-cro-tonolactone in 23% yield and -hydroxy-y-butyrolactone in 28% yield. The formation of y-crotonolactone in 15% yield has also been reported from pyrolysis of 2,5-diacetoxy-2,5-dihydrofuran at 480-500 . ... 

Only three constituents have been reported from Broussonetia zeylanica, all by a group at the University of Peradeniya in Sri Lanka [89-91]. A major alkaloid, 8-hydroxyquinoline-4-carbaldehyde (55), was identified as an antimicrobial agent active against Staphyllococus aureus and Candida albicans (the levels of activity were not specified) [89] and then two minor compounds, 3,4 -dihydroxy-2,3 -bipyridine (56) and 3,4-bis(8-hydroxyquinolin-4-yl)-y-butyrolactone (broussonetine, 57), were reported, Fig. (10) [90,91]. However, the structure of 3,4 -dihydroxy-2,3 -bipyridine (56) was revised to 8-hydroxyquinoline-4-carbaldehyde oxime (58) by synthesis [92,93]. Also, it was noted that an artefactual origin of this oxime (58) could not be ruled out due to the presence of the corresponding aldehyde (55) [93]. 

Dihydroxy-y-butyrolactones.1 -y-Butenolides (1) are oxidized by KMn04 in the presence of a crown ether (dicyclohexyl- 18-crown-6) to mixtures of the cis-diols 2 and 3 with some preference for the former. The stereoselectivity is influenced by the substituent at the -y-position. It is highest with bulky -y-alkoxymethyl groups and lowest with alkyl substituents. 

Two minor alkaloids were also isolated from B. zeylanica timber. The structure of one of these, C1oN8N202, mp 223-224°C, was revised from 3,4-dihydroxy-2,2 -bipyridine (18) to 8-hydroxyquinoline-4-carbaldehyde oxime (2) based on synthetic, NMR and nuclear overhauser effect (NOE) difference NMR spectroscopic evidence (19). Natural occurrence of oximes, although rare in higher plants, is not without precedence, and the essential oil of Ruta montana L. has been reported to contain the bis-oxime of 3,4-hexanedione (20). The structure of the nonpolar minor alkaloid broussonetine, C22H16N2O4, mp 238-239°C, was elucidated as 3,4-bis(8-hydroxyquinolin-4-yl)-y-butyrolactone (4) (21). 

Using Upjohn condition (OsOi-NMO). The utility of the Upjohn protocol for the dihydroxylation was recently demonstrated in the synthesis of bicyclic analogues of pentopyranoses, (-)-anisomycin, trisubstituted y-butyrolactone, 6-bromo-4-(l,2-dihydroxyethyl)-7-hydroxycoumarine (Bhc-diol) as a photoremovable protecting group, 3,4-dihydroxy-2-(3-methylbut-2-enyl)-3,4-dihydronaphthalen-l(2//)-one, benzo-[c]pyrano[3,2-/z]acridin-7-ones, both enantiomers of conduri-tol C tetraacetate and of mei o-conduritol-D-tetraacetate. ... 

Bryan R F, Shen M S 1978 Gnidifolin ran5-2-(2,4-dihydroxy-3-methoxybenzyl)-3-(4 -hydroxy-3 -methoxybenzyl)-butyrolactone). Acta Cryst B34 327-329... 

Hougaard, L., Anthoni, U., Christophersen, C., and Nielsen, P.H. (1991b) Two new diterpenoid dihydroxy-y-butyrolactones from Bijurcaria bijurcata (Cystoseiraceae). Tetrahedron Lett., 32, 3577-3578. 

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