References
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- Raffauf , F. , Huang , Pih-Kuei C. , Le Quesne , P. W. , Levery , S. B. and Brenna , T. F. 1975 . J. Am. Chem. Soc. , 97 : 6884 In addition to jatrophone an increasing number of antitumor agents possessing the 3(2H)-furanone ring system have recently been uncovered, see for example and references cited therein
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- The structure assigned to each compound was in accord with its infrared and 220 MHz nmr spectra. Analytical samples of each new compound, obtained by preparative vapor phase chromatography (vpc) gave C and H H H H combustion analysis within 0.4% of theory
- All yields reported are vpc calibrated. Isolated yields were 5–7% lower
- House , H. O. , Chu , C.-Y. , Wilkins , J. M. and Umen , M. J. 1975 . J. Org. Chem. , 40 : 1460 In contrast to the facility with which lithium dimethyl and lithium di-n-butyl cuprate underwent conjugate addition with 1, the analogous reaction of lithium diphenyl cuprate proved somewhat erratic, requiring rather precise experimental conditions for optimal yield. For this reason we report below a detailed procedure for the preparation of 4. To 204.8 mg (0.997 mmol) of the freshly prepared complex of cuprous bromide (Merck)-dimethyl sulfide [ resulting clear solution was cooled to -23[ddot] C and 1.2 ml of 1.75 M phenyl lithium (2.1 mmol) was added over a period of 5 min. After stirring 20 min. 49.5 mg (0.442 mmol) of furanone 1 in 1.5 ml of Et2O was added dropwise. The resulting solution was then maintained at -23 to -25[ddot] C with stirring for 1 hr, after which the mixture was brought to room temperature and stirred for an additional hr. Usual work-up with 10% aq. NH4OH gave after removal of solvent a 58% yield of 4. was added 1.0 ml of Me2S and 1.5 ml Et2 The O
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- Bernstein , S. and Littell , R. 1960 . J. Am. Chem. Soc. , 82 : 1235
- Brandt , C. W. , Taylor , W. I. and Thomas , B. R. 1954 . J. Chem. Soc. , : 3245
- Parker , W. , Raphael , R. A. and Wilkinson , D. I. 1958 . J. Chem. Soc. , : 3871
- In connection with our studies directed at developing a general approach to 3(2H)-furanone derivatives, we have demonstrated that bullatenone 5 can be prepared in 84% yield via an intramolecular base catalyzed cyclization of the benzoate ester of 3-hydroxy-3-methyl-2-butanone. Details of this study will be forthcoming in the near future