Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Synthesis of Hydroxyalkyl Heterocycles by Ring Transformation of Spiroepoxy Lactones with Binucleophiles Andreas Otto, Jürgen Liebscher*Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Str. 2, 12489 Berlin, GermanyFax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de; Recommend Article Abstract Buy Article All articles of this category Abstract Spiroepoxy lactones 2 and 3 were obtained by epoxidation of α-alkylidenelactones 1 with dimethyldioxirane. Reaction of spiroepoxy lactones 2 with binucleophiles gave access to a number of hydroxyalkyl heterocycles with interesting substituent patterns. Depending on both the kind of substituent at the oxirane ring as well as the type of the binucleophile, the spiroepoxy lactones react either as C3 or as C2 bielectrophilic building blocks giving 4-, 6- and 7-membered partially saturated N-and S-heterocycles 5, 6, 8, 9, 11 and 13. Key words epoxidations - ring transformation - thiazepinones - diazepinones - 1,4-thiazinones - benzothiopyranones - β-lactams Full Text References References 1 Otto A. Ziemer B. Liebscher J. Eur. J. Org. Chem. 1998, 2667 2 Otto A. Ziemer B. Liebscher J. Synthesis 1999, 965 3 Otto A. Abegaz B. Ziemer B. Liebscher J. Tetrahedron: Asymmetry 1999, 10: 3381 4 Otto A. Liebscher J. J. Heterocycl. Chem. 2000, 37: 891 5 Woydowski K. Ziemer B. Liebscher J. J. Org. Chem. 1999, 64: 3489 6 Woydowski K. Liebscher J. Tetrahedron 1999, 55: 9205 7 Woydowski K. Liebscher J. Synthesis 1998, 1110 8 Woydowski K. Ziemer B. Liebscher J. Tetrahedron: Asymmetry 1998, 9: 1231 9 Woydowski K. Liebscher J. J. Prakt. Chem. 1998, 340: 567 10 Woydowski K. Fleischhauer J. Schiffer J. Liebscher J. J. Chem. Soc., Perkin Trans. 1 1999, 149 11 Bohlmann F. Fritz U. King RM. Robinson H. Phytochemistry 1981, 20: 743 12 Fischer NH. Lee IY. Fronczek FR. Chiari G. Urbatsch LE. J. Nat. Prod. 1984, 47: 419 13 Sohoni JS. Rojatkar SR. Kulkarni MM. Dhaneshwar NN. Tavale SS. Gururow TN. Nagasampagi BA. J. Chem. Soc., Perkin Trans. 1 1988, 157 14 Borges del Castillo J. Manresa Ferrero MT. Rodriguez Luis F. Rodriguez Ubis JC. Vazquez Bueno P. Rev. Latinoam. Quim. 1984, 15: 96 ; Chem. Abstr. 1985, 102, 182384 15 Trost BM. Arndt HC. J. Org. Chem. 1973, 38: 3140 16 White JD. Bremner JB. Dimsdale MJ. Garcea RL. J. Am. Chem. Soc. 1971, 93: 281 17 Shibata I. Yamasaki H. Baba A. Matsuda H. J. Org. Chem. 1992, 57: 6909 18 Guseinov FI. Tagiev SSh. Moskva VV. Zh. Org. Khim. 1995, 31: 96 19 Murray AW. Reid RG. Synthesis 1985, 35 20 Strobach DR. Carbohydr. Res. 1971, 17: 457 21 Yamauchi S. Kinoshita Y. Biosci., Biotech. Biochem. 1998, 62: 1726 22 Bertounesque E. Millal F. Meresse Ph. Monneret C. Tetrahedron: Asymmetry 1998, 9: 2999 23 Akbutina FA. Sadretdinov IF. Vasile’va EV. Miftakhov MS. Russ. J. Org. Chem. 2000, 36: 1823 24 Stachel HD. Poschenrieder H. Burghard H. Z. Naturforsch. 1980, 35B: 724 25 Peng H. Kim D.-I. Sarkaria JN. Cho Y.-S. Abraham RT. Zalkow LH. Bioorg. Med. Chem. 2002, 10: 167 26 Bartels A. Jones PG. Liebscher J. Tetrahedron: Asymmetry 1995, 6: 1539 27 Panfiel J. Chmielewski M. Belzencki C. Heterocycles 1986, 6: 1609 28 Pätzel M. Ushmajev A. Liebscher J. Synthesis 1993, 525 ; and references cited therein 29 Adam W. Bialas J. Hadjiarapoglou L. Chem. Ber. 1991, 124: 2377 30 Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-205880. Copies of the data can be obtained free of charge on apllication to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.
