Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York A Facile Synthesis of 1,1′-Spirobi(3H,3′H)isobenzofurans Margaret A. Brimble*, Caryn V. BurgessDepartment of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New ZealandFax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract The synthesis of a series of aryl 5,5-spiroketals containing a 1,1′-spirobi(3H,3′H)isobenzofuran ring system is reported. The key step involves addition of an aryllithium derived from a protected bromobenzyl alcohol to a phthalide; this is followed by deprotection of the benzyl alcohol and acid-catalysed cyclisation. Key words spiro compounds - ketals - phthalides - lithium compounds - heterocycles Volltext Referenzen References 1 Mead KT. Brewer BN. Curr. Org. Chem. 2002, 7: 227 2a Brockmann H. Lenk W. Schwantje G. Zeeck A. Tetrahedron Lett. 1966, 3525 2b Brockmann H. Lenk W. Schwantje G. Zeeck A. Chem. Ber. 1969, 102: 126 2c Brockmann H. Zeeck A. Chem. Ber. 1970, 103: 1709 3 Ueno T. Takahashi H. Oda M. Mizunuma M. Yokoyama A. Goto Y. Mizushina Y. Sakaguchi K. Hayashi H. Biochemistry 2000, 39: 5995 4 Goldman ME. Salituro GS. Bowen JA. Williamson JM. Zink L. Schleif WA. Emini EA. Mol. Pharmacol. 1990, 38: 20 5a Qin D. Ren RX. Siu T. Zheng C. Danishefsky SJ. Angew. Chem. Int. Ed. 2001, 40: 4709 5b Siu T. Qin D. Danishefsky SJ. Angew. Chem. Int. Ed. 2001, 40: 4713 6a Capecchi T. de Koning CB. Michael JP. Tetrahedron Lett. 1998, 39: 5429 6b Capecchi T. de Koning CB. Michael JP. J. Chem. Soc., Perkin Trans. 1 2000, 2681 7 Zhou G. Zheng D. Da S. Li Y. Tetrahedron Lett. 2006, 47: 3349 8a Waters SP. Fennie MW. Kozlowski MC. Tetrahedron Lett. 2006, 47: 5409 8b Waters SP. Fennie MW. Kozlowski MC. Org. Lett. 2006, 8: 3243 9 Lindsey CC. Wu KL. Pettus TRR. Org. Lett. 2006, 8: 2365 10 Sörgel S. Azap C. Reissig H.-U. Org. Lett. 2006, 8: 4875 11 Tsang KY. Brimble MA. Bremner JB. Org. Lett. 2003, 5: 4425 12 Brimble MA. Flowers C. Trzoss M. Tsang KY. Tetrahedron 2006, 62: 5883 13 Vertsey L. Kurz M. Paulus EF. Schummer D. Hammann P. J. Antibiot. 2001, 54: 354 14 Verhage M. Hoogwater DA. Reedijk J. van Bekkum H. Tetrahedron Lett. 1979, 14: 1267 15 Epsztajn J. Jozwiak A. Szczesniak AK. J. Chem. Soc., Perkin Trans. 1 1998, 2563 16 Kamaki K. Namiki T. Kawashima E. Nucleosides, Nucleotides Nucleic Acids 2003, 22: 469 17 McAlees AJ. McCrindle R. Sneddon DW. J. Chem. Soc., Perkin Trans. 1 1977, 2030 18 Paradkar MV. Kukarni SA. Joesph AR. Ranade AA. J. Chem. Res., Synop. 2002, 364 19 Carreira EM. Du Bois J. J. Am. Chem. Soc. 1994, 116: 10825 20 Van Rijn PE. Mommers S. Visser RG. Verkruijsse HD. Brandsma L. Synthesis 1981, 459 21 Ramesh C. Ravindranath N. Das B. J. Org. Chem. 2003, 68: 7101 22 Larock RC. Doty MJ. Cacchi S. J. Org. Chem. 1993, 58: 4579 23 Merlic CA. Aldrich CC. Albaneze-Walker J. Saghatelian A. Mammen J. J. Org. Chem. 2001, 66: 1297 24 Breton GW. J. Org. Chem. 1997, 62: 8952
