P. DeShong et al. / Journal of Organometallic Chemistry 593–594 (2000) 49–62
61
[7] K. Jewers, A.H. Manchanda, H.M. Rose, in: G.P. Ellis, G.B.
West (Eds.), Progress in Medicinal Chemistry, vol. 9, Elsevier,
New York, 1973, pp. 1–63.
[8] T. Matsumoto, H. Kakigi, K. Suzuki, Tetrahedron Lett. 32
(1991) 4337–4340.
[9] T. Matsumoto, M. Katsuki, H. Jona, K. Suzuki, Tetrahedron
Lett. 30 (1989) 6185–6188.
[10] S.J. Danishefsky, B.J. Uang, G. Quallich, J. Am. Chem. Soc. 107
(1985) 1285–1293.
[11] M.A. Tius, J. Gomez–Galeno, X. Gu, J.H. Zaidi, J. Am. Chem.
Soc. 113 (1991) 5775–5783.
[12] K. Krohn, W. Baltus, Tetrahedron 44 (1988) 49–54.
[13] M.E. Jung, Y.H. Jung, Tetrahedron Lett. 29 (1988) 2517–2520.
[14] J. Farkas, Z. Flegelova´, F. Sorm, Tetrahedron Lett. 13 (1972)
2279–2280.
[15] S. DeBernardo, M. Weigele, J. Org. Chem. 41 (1976) 287–290.
[16] J.G. Buchanan, A. Stobie, R.H. Wightman, J. Chem. Soc.
Chem. Commun. (1980) 916–917.
[17] N. Karagiri, K. Takashimi, T. Haneda, T. Kato, J. Chem. Soc.
Perkin Trans. 1 (1984) 553–560.
[18] P.C. Srivastava, R.K. Robins, J. Med. Chem. 26 (1983) 445–
448.
[19] P.C. Srivastava, M.V. Pickering, L.B. Allen, D.G. Streeter, M.T.
Campbell, J.T. Witkowski, R.W. Sidwell, R.K. Robins, J. Med.
Chem. 20 (1977) 256–262.
[20] P. DeShong, G.A. Slough, V. Elango, G. Trainor, J. Am. Chem.
Soc. 107 (1985) 7788–7790.
[21] P. DeShong, G.A. Slough, V. Elango, Carbohydr. Res. 171
(1987) 342–345.
[22] P. DeShong, D.R. Sidler, G.A. Slough, Tetrahedron Lett. 28
(1987) 2233–2236.
[23] P. DeShong, G.A. Slough, A.L. Rheingold, Tetrahedron Lett. 28
(1987) 2229–2232.
brown precipitate (an oxidized manganese by-product).
After 1 h the suspension was filtered, concentrated in
vacuo, and the resulting residue was purified by column
chromatography eluting with 5% ethyl acetate/hexanes
to give 0.262 g (65%) of butenolide 55 as a white solid
and 139 mg (35%) of keto-sulfone 52 as a white solid.
Sulfone 52 was recrystallized from hexanes to give
white crystals. Rf=0.10 (25% ethyl acetate/hexanes).
IR (CCl4): 1738, 1325, 1156. 1H-NMR (200 MHz,
CDCl3): l 7.90–7.85 (m, 2H), 7.62–7.45 (m, 3H), 7.30–
7.10 (m, 20H), 4.78 (s, 2H), 4.75–4.50 (m, 6H), 4.33–
4.15 (m, 7H), 3.30–3.12 (m, 2H), 3.10–2.95 (m, 2H).
13C-NMR (50 MHz, CDCl3): l 200.3, 139.3–139.3,
133.6, 129.3, 128.4–127.7, 86.2, 82.6, 79.3, 78.7, 78.0,
75.3, 74.8, 74.5, 73.7, 69.4, 50.4, 32.6. MS m/z (HR):
Calc. for C43H44O8S 720.2757. Found 720.2948.
Furanone 55 was recrystallized from hexanes to give
white crystals. Rf=0.15 (25% ethyl acetate/hexanes).
1
IR (CCl4): 1766, 1495. H-NMR (200 MHz, CDCl3): l
7.27–7.10 (m, 20H), 6.77 (dd, J=1.4, 5.7 Hz, 1H), 5.92
(dd J=1.4, 5.8 Hz, 1H), 5.11 (d, J=1.4 Hz, 1H),
4.95–4.72 (m, 6H), 4.53 (dd, J=4.2, 10.2 Hz, 2H), 4.43
(s, 2H), 3.70–3.52 (m, 4H), 3.41–3.30 (m, 1H). 13C-
NMR (50 MHz, C6D6): l 171.8, 151.3, 139.2, 139.2,
138.4, 128.4–127.6, 122.2, 87.5, 82.2, 79.8, 78.8, 78.3,
77.8, 75.4, 74.9, 74.2, 73.7, 69.1. MS m/z (HR): Calc.
for C38H37O7 605.2540. Found 605.2414. Calc. for
C31H31O7 (M–Bn) 515.2070. Found 515.2011.
[24] P. DeShong, D.R. Sidler, J. Org. Chem. 53 (1988) 4892–4894.
[25] P. DeShong, D.R. Sidler, P.J. Rybczynski, G.A. Slough, A.L.
Rheingold, J. Am. Chem. Soc. 110 (1988) 2575–2585.
[26] P. DeShong, D.R. Sidler, P.J. Rybczynski, A.A. Ogilvie, W. von
Philipsborn, J. Org. Chem. 54 (1989) 5432–5437.
[27] P. DeShong, G.A. Slough, D.R. Sidler, P.J. Rybczynski, W. von
Philipsborn, R.W. Kunz, B.E. Bursten, T.W. Clayton Jr.,
Organometallics 8 (1989) 1381–1388.
Acknowledgements
P.D. thanks the National Institutes of Health for
generous financial support of this project. We also
acknowledge financial support from Tektronix, and
Lederle Laboratories. W.v.P. thanks the Swiss National
Science Foundation and the Dr Helmut Legerlotz
Stiftung for generous funding and Dr V. Torochesh-
nikov for preliminary experiments and valuable advice.
[28] P. DeShong, P.J. Rybczynski, J. Org. Chem. 56 (1991) 3207–
3210.
[29] L.J. Smith, P. DeShong, unpublished results.
[30] G.L. Trainor, B.E. Smart, J. Org. Chem. 48 (1983) 2447–2448.
[31] A. Rosenthal, H.J. Koch, Tetrahedron Lett. 8 (1967) 871–874.
[32] K.H. Do¨tz, W. Straub, R. Ehlenz, K. Peseke, R. Meisel, Angew.
Chem. Int. Ed. Engl. 34 (1995) 1856–1858.
[33] K.H. Do¨tz, R. Ehlenz, D. Paetsch, Angew. Chem. Int. Ed. Engl.
36 (1997) 2376–2378.
References
[34] P.L. Bock, D.J. Boschetto, J.R. Rasmussen, J.P. Demers, G.M.
Whitesides, J. Am. Chem. Soc. 96 (1974) 2814–2825.
[35] E.D. Soli, P. DeShong, unpublished results.
[36] T.A. Lessen, P. DeShong, unpublished results.
[37] R.U. Lemieux, J.-I. Haymi, Can. J. Chem. 43 (1965) 2162–2173.
[38] R.U. Lemieux, K.B. Hendriks, R.V. Stick, K. James, J. Am.
Chem. Soc. 97 (1975) 4056–4062.
[39] G.B. Anderson, P. DeShong, unpublished results.
[40] T.X. Le, P. DeShong, unpublished results.
[41] V.M.S. Gil, W. von Philipsborn, Magn. Reson. Chem. 27 (1989)
409–430.
[42] P. DeShong, T.A. Lessen, T.X. Le, G. Anderson, D.R. Sidler,
G.A. Slough, W. von Philipsborn, M. Vo¨hler, O. Zerbe, in: G.
Thatcher (Ed.), Anomeric Effect and Associated Stereoelectronic
Effects, vol. ACS Series 539, American Chemical Society, Was-
ington, DC, 1993, pp. 227–239.
[1] A. Rosenthal, in: M.L. Wolfrom, R.S. Tipson (Eds.), Advances
in Carbohydrate Chemistry, vol. 23, Academic Press, New York,
1968, pp. 59–114.
[2] R.J. Suhadolnik, Nucleosides as Biological Probes, Wiley Inter-
sciences, New York, 1979.
[3] J. Goodchild, in: P.G. Sammes (Ed.), Topics in Antibiotic
Chemistry, vol. 6, Halsted, New York, 1982, pp. 99–227.
[4] S. Hannessian, A.G. Pernet, Adv. Carbohydr. Chem. Biochem.
33 (1976) 111.
[5] J.G. Buchanan, in: W. Herz, H. Grisebach, G.W. Kirby (Eds.),
Progress in the Chemistry of Organic Natural Products, vol. 44,
Springer–Verlag, New York, 1983, pp. 243–299.
[6] J.G. Buchanan, R.H. Wightman, in: P.G. Sammes (Ed.), Topics
in Antibiotic Chemistry, vol. 6, Halsted, New York, 1982, pp.
229–339.