Recent Developments in γ-Lactone Synthesis (original) (raw)
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Recent Developments in γ-Lactone Synthesis
Mini-Reviews in Organic Chemistry, 2009
In recent years, several classes of biologically active molecules containing the -lactone ring, pesticides, plant and fungal growth inhibitors, and antibiotics have been found. Thus the synthesis of substituted dihydrofuran-2(3H) ones is a continuously developing area. Few general synthetic approaches to their stereoselective synthesis with broad structural variety are known. This article reviews the latest developments in the synthesis of -butyrolactones. We focus on the ring-closing steps and pay special attention to how different authors obtain the correspondent 4-hydroxycarbonyl compound; an acyclic synthon for the -lactone ring.
Recent Developments in ?-Lactone Synthesis
Mini Rev Org Chem, 2009
In recent years, several classes of biologically active molecules containing the -lactone ring, pesticides, plant and fungal growth inhibitors, and antibiotics have been found. Thus the synthesis of substituted dihydrofuran-2(3H) ones is a continuously developing area. Few general synthetic approaches to their stereoselective synthesis with broad structural variety are known. This article reviews the latest developments in the synthesis of -butyrolactones. We focus on the ring-closing steps and pay special attention to how different authors obtain the correspondent 4-hydroxycarbonyl compound; an acyclic synthon for the -lactone ring.
European Journal of Medicinal Chemistry, 2006
The synthesis of a series of α-methylene-γ-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and α,β-unsaturated-δ-lactones (compounds 19 −23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different antiproliferative properties against cultured human tumor cell lines with their IC 50 values ranging from 0.88 to > 20.00 μM.
A short approach to trisubstituted γ-butyrolactones
Tetrahedron Letters, 2006
Furan derivatives R 0060 A Short Approach to Trisubstituted γ-Butyrolactones.-It is demonstrated that the dihydroxylation of unsaturated syn-aldols occurs with good levels of diastereoselectivity to yield the target compounds required as structural units in pharmacologically interesting natural products.-(DIAS*, L. C.; DE CASTRO, I.
Tetrahedron Letters, 1990
4-Cyclohexyl 3,3_disubstituted oxetan-2-ones rearrange under Lewis acid catalysis to afford trans.-fused cycloheptano butyrolactones. A host of natural products, most notably the guaianolide and pseudoguaiaqolides, contain a butyrolactone which is trans-fused to a cycloheptane ring, and2a number of ingenious techniques have been reported for their synthesis. The primary difficulties in guaianolide synthesis reside in the construction of the seven-membered ring, complete with stereochemically defined substi-tuents, and fixation of the trans lactone ring in a highly stereoselective manner. An attractive approach to the synthesis of these molecules would involve the functionalization of a cyclohexane ring, where stereochemical control is considerably more facile, followed by expansion to the cycloheptyl homolog with simultaneous formation of the required translactone. Mars?all's elegant cyclopropylcarbinol solvolysis scheme exemplifies this strategy. We now wish to report a short, conceptually unique synthetic method which accomplishes the construction of cycloheptano trans-fused butyrolactones in three steps from six-membered carbocyclic precursors. We have recently reported a number of useful lactzne syntheses based on the rearrangement of alkyl-or cycloalkyl B-la&ones. As illustrated below, cyclohexyl A-lactones 2 (derived in two steps from the aldehyde 1) are transformed into Spiro butyrolactones 3 when the ring is situated trans to a 3-substituent, since rotation of the cyclohexyl-la&one bond is relatively a=RCHtiCO& b=PhSO&I; c=MgBr, 6617 administered by the American Chemical Society, in addition to the Research Corporation, for support of this work. The 300 MHz NMR instrument was acquired with the help of the National Science Foundation (CHE-8815619). 1. 25.0, 24.9, 22.8, 22.7 ppm; TLC (CH2C12) Rf 0.41. Canonne, P.; Belanger, D.; Lemay, G.; Foscolos, G.B. J. Org. Chem. 1981, 46, 3091.
Facile and stereoselective synthesis of fused γ-butyrolactones of carbohydrates
Tetrahedron Letters, 1998
Photocycloadducts obtained from different homochiral butenolides and vinylene carbonate are shown to be useful precursors of fused "f-butyrolactones of carbohydrates. Cyclobutanes 1 have been used successfully by us as precursors of cyclobutane containing natural products such as (+)-grandisol [1]. These bicyclic compounds are easily available by [2+2] photocycloaddition of ethylene to 2(5H)-furanones [2-3]. In this reaction two cycloadducts are obtained: the anti and the syn isomers. Since only the anti cycloadduct relates to the natural product we have studied extensively the diastereofacial course of the [2+2]