Y-butanolides

A similar transformation can be carried out under milder conditions by taking advantage of silyl ketene acetals, a masked form of the earboxylate dianion. When epichlorohydrin 53 was treated with the ketene acetal 79 in the presence of titanium(IV) chloride, a regioseleetive epoxide ring opening occurs at the less substituted carbon. Treatment of the crude reaction mixture with catalytic p-toluenesulfonic acid promoted a lactonization to the y-butanolide 80 in high overall yield <04T8957>. 

Miyabe and Naito revealed a synthesis of y-lactones through sequential radical reaction of acrylates bearing oxime functionality with alkyl radicals generated from iodoalkane and efliyl radical [62]. That is, addition reaction of isopropyl radical to acrylate moiety of substrate 86 and the following cyclization to oxime functionality produced the p-amino-y-butanolide 87 with good diastereoselectivitiy (Scheme 40). 

V. Maslak, R. Matovic, R.N. Saici6, Reaction of silyl ketene acetals with epoxides a new method for the synthesis of y-butanolides. Tetrahedron 60 (2004) 8957-8966. 

In addition, other systems of nomenclature for AHLs have also appeared in the literature describing them as derivatives of furanone, y-butyrolactone or 4-butanolide. For example, the above V.fischeri autoinducer can also be named as (S)-N-(3-oxohexanoyl)-3-aminodihydro-2(3H)-furanone,(S)-a-(3-oxohexa-noyl)amino-y-butyrolactone or (S)-2-(3-oxohexanoyl)amino-4-butanolide (another IUPAC name) [27]. 

Intramolecular addition can occur when nucleophilic substituents are suitably positioned as in Eq. 14 [88]. When the latter electrolysis is conducted in CH2CI2/BU4 NCI, 75% of the chloro-y-lactone are obtained. Electrolysis of ( )-5-phenyl-4-pentenoic acid affords a 4-(phenyl-methoxymethyl) -4-butanolide [89]. 

Antibiotic production and morphological differentiation (formation of aerial mycelium and sporulation) in Streptomyces species and in some other actinomycetes is regulated by small signaling molecules called y-butyrolactones or butanolids. These quorum-sensing signals bind to... 

Morino, A., Kuwahara, Y., Matsuyama, S. and Suzuki, T. (1997). ( ,)-2-(4/-Methyl-3 -pentenylidene)-4-butanolide, named /i-acariolidc a new monoterpene lactone from the mold mite, Tyrophagus putrescentiae (Acarina Acaridae). Bioscience, Biotechnology and Biochemistry 61 1906-1908. 

Metalated /V -diisopropyl 2-alkenyl carbamates (130) are reported to be successfully utilized to prepare, with high -y-regioselectively (equation 51), 4-hydroxyalkenyl carbamates like (131), which are useful intermediates in the synthesis of substituted 4-butanolides. ... 

Figure 2. Examples of Various Lactone Moieties in Annonaceous Acetogenins an a, p-Unsaturated-y-lactone [Annonin I (4)], a C(4)-Hydroxylated a, P-Unsaturated-y-lactone [Bullatacin (5)], a Rearranged Acetonyl Butanolide [Bullatacinone (6)], and a Saturated p-Hydroxy-y-lactone [Itrabin (7)].

The decreased Internet availability of kits to make GHB has been accompanied by an increased availability of chemical precursors to GHB as well as GHB analogs. Also available in gyms and health food stores, these substances include y-butyrolactone (GBL) and 1,4-butanediol. GBL is converted in the body to GHB. Labels of marketed products may use unfamiliar synonyms to disguise the actual content. GBL is also known by the chemical names 2(3H)-furanone dihydro, butyrolactone, 4-butyrolactone, dihydro-2(3H)-furanone, 4-butanolide, 2(3H)-furanone, dihydro, tetrahydro-2-fura-none, and butyrolactone-y. 

G.l) (G.l) 2(3//)-Furanone dihydro-, butano-4-lactone, tetrahydrofuran-2-one, 4-butanolide, 4-hydroxybutanoic acid lactone, y-butyrolactone 196-48-0] FEMA 3291... 

The spiro-dihydrofuran (61) is converted into the cyclobutane derivative (62) under the influence of trifluoroacetic acid. The lithium dienolate (64), derived from the furanone (63), yields solely y-alkylated products on treatment with alkyl halides. Thermolysis of the t-butylperoxybutenolide (65) produces about equal amounts of the hydroxy-furanone (67) and the indenone (68), presumably via the oxide radical (66). Attack of iodide ion on the salt (69) results in the formation of methyl iodide, butanolide, and (surprisingly) methyl 4-iodobutanoate. A description of a study of the photochemical rearrangement of the tetrahydrofurans (70) to the bicyclic oxetans (71) has been presented. ... 

Synonyms BLO 1,2-Butanolide 1,4-Butanolide Butyric acid iactone a-Butyroiactone y-Butyroiactone Butyryi iactone 4-Deoxytetronic acid Dihydro-2(3H)-furanone GBL 4-Hydroxybutanoic acid iactone y-Hy-droxybutyric acid cyciic ester 4-Hydroxybutyric acid y-iactone y-Hy-droxybutyric acid iactone y-Hydroxybutyroiactone Tetrahydro-2-furanone... 

A mixture of bis(3-benzyloxybenzylidene)succinic acid and a little octacarbonyltetra-hydridotetrakis(tri- -butylphosphine)tetraruthenium in toluene pressurized to 150-80 bar with at room temp, in a Hastelloy C steel rocking autoclave, and heated in an oil bath at 180 maintaining the pressure at 200 bar with additional H2 until reaction complete (ca. 48 h)2,3-bis(3-benzyloxybenzyl)-4-butanolide. Y 93% (75% trans). F.e.s. M. Bambagiotti-Alberti et al.. Heterocycles 27, 2185-96 (1988). 

Mizuno K, Sakuda S, Nihira T, Yamada Y. Enzymatic resolution of Z-acyl-J-hydroxymcthyl-4-butanolide and preparation of optically active IM-2, the autrxegulator from Screptomyces... 

Hashimoto K. Nihira T, Yamada Y. Distribution of virginiae butanolides and IM-2 in the genus Sirepiomyces. J Ferment Bioeng 1992 73 61-65. 

Sakuda S, Higashi A, Tanaka S, Nihira T, Yamada Y. Biosynthesis of virginiae butanolide A, a butyrolactone autoregulator from Streptomyces. J Am Chem Soc 1992 114 663-668. 

Deoxypentonic acid y-lactone, 9CI. 2-Hydroxy-4-hydroxymethyl-4-butanolide [74243-47-3]... 

Synonyms Dihydro-2(3H)-fiiranone 1,2-butanolide 1,4-butanolide 3-hydroxybutyric acie lactone y-hydroxybutyrolactone y-hydoxybutyric acid lactone Trade Names ... 

The relationship of the )9,y-substituents in dihydromahuba lactones of series A was determined to be threo and that in the series B as erythro by the LIS NMR techniques (71). Mahuba lactones carry an exomethylene group at C-5 of the butanolide ring. The long alkyl side chains in these lactones are in the same alkane-alkene-alkyne-type relationship as in litsenolides. Isodihydromahubano-lide 23-A (15) and -B (22), mahubanolide-23 (29), and isomahubanolide-23 (30) are larger than the rest by two carbon units. 

Rubrenolide (39) (mp 100 °C, [aJo +21°) and rubrynolide (40) (mp 88 °C, [alo +21°) from Nectandra rubra (Lauraceae) are another type of y-lactones of alkene-alkyne pair (39). In these compounds, the alkene or alkyne substituent is attached to C-4 of the butanolide ring. 

Trunk wood of Mezilaurus synandra one of the species of Mezilaurus belonging to the same subtribe as Clinostemon, was shown to contain a similar y-lactone, (2/ ,3, 4S)-2-dodec-cu-enyl-3-hydroxy-4-methylbutanolide (41) (mp 72-76°C, [a]o -7.5 ) (115). The butenolide (42) from the same source is considered to be an artificial dehydration product of the 3-hydroxy-lactone (41). All of the above aliphatic y-lactones were isolated from Lauraceae 2-hy-droxy-4-(heptadec-8 -enyl)butanolide (43) obtained as an oil from the bark of Garcinia mannii (Guttiferae) is the only compound of this type found in other families (53). 

---