Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart ˙ New York Formal Synthesis of (R)-(+)-Lasiodiplodin Yange Huang, Adriaan J. Minnaard*, Ben L. Feringa*Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The NetherlandsFax: +31(50)3634278; e-Mail: a.j.minnaard@rug.nl; e-Mail: b.l.feringa@rug.nl; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A catalytic approach is reported for the enantioselective synthesis of (R)-(+)-lasiodiplodin methyl ether using asymmetric hetero allylic alkylation as the key step. Key words formal synthesis - lasiodiplodin - asymmetric allylic alkylation - Suzuki coupling - ring-closing metathesis Volltext Referenzen References 1a Delmotte P. Delmotte-Plaquee J. Nature 1953, 171: 344 1b Stob M. Baldwin RSK. Gillette G. Andrews F. Tuite NJ. Nature 1962, 196: 1318 1c Ellestad GA. Lovell FMN. Perkinson A. Hargreaves RT. McGahren WJ. J. Org. Chem. 1978, 43: 2339 1d Nair MSR. Carey ST. Tetrahedron Lett. 1980, 21: 2011 2a Aldridge DC. Galt S. Giles D. Turner B. J. Chem. Soc. C 1971, 1623 2b Cambie RC. Lal AR. Rutledge PS. Woodgate PD. Phytochemistry 1991, 30: 287 2c Lee K.-H. Hayashi N. Okano M. Hall IH. Wu R.-Y. McPhail AT. Phytochemistry 1982, 21: 1119 3 Xin-Sheng Y. Ebizuka Y. Noguchi H. Kiuchi F. Litaka Y. Sankawa U. Seto H. Tetrahedron Lett. 1983, 2407 4a Gerlach H. Thalmann A. Helv. Chim. Acta 1977, 60: 2866 4b Danishefsky SJ. Etheredge SJ. J. Org. Chem. 1979, 44: 4716 4c Takahashi T. Kasuga K. Tsuji J. Tetrahedron Lett. 1978, 4917 4d Braun M. Mahler U. Houben S. Liebigs Ann. Chem. 1990, 513 4e Jones GB. Huber RS. Synlett 1993, 367 4f Fink M. Gaier H. Gerlach H. Helv. Chim. Acta 1982, 65: 2563 4g Solladie G. Rubio A. Carreno MC. Ruano JLG. Tetrahedron: Asymmetry 1990, 1: 187 4h Bracher F. Schulte B. J. Chem. Soc., Perkin Trans. 1 1996, 2619 4i Fürstner A. Seidel G. Kindler N. Tetrahedron 1999, 55: 8215 4j Fürstner A. Thiel OR. Kindler N. Bartkowska B. J. Org. Chem. 2000, 65: 7990 4k Kashima T. Takahashi K. Matsuura H. Nabeta K. Biosci., Biotechnol., Biochem. 2009, 73: 1118 4l Kashima T. Takahashi K. Matsuura H. Nabeta K. Biosci., Biotechnol., Biochem. 2009, 73: 2522 4m Fürstner A. Kindler N. Tetrahedron Lett. 1996, 37: 7005 5 Geurts K. Fletcher SP. Feringa BL. J. Am. Chem. Soc. 2006, 128: 15572 6 Abe H. Nishioka K. Takeda S. Arai M. Takeuchi Y. Harayama T. Tetrahedron Lett. 2005, 46: 3197 7 Chemler SR. Trauner D. Danishefsky SJ. Angew. Chem. Int. Ed. 2001, 40: 4544 8 Wong LS.-M. Sherburn MS. Org. Lett. 2003, 5: 3603 9 Fürstner A. Bindl M. Jean L. Angew. Chem. Int. Ed. 2007, 46: 9275 10 Olah GA. Nojima M. Kerekes I. Synthesis 1973, 487 11 Crimmins MT. Tabet EA. J. Am. Chem. Soc. 2000, 122: 5473 12 Quinn KJ. Curto JM. McGrath KP. Biddick NA. Tetrahedron Lett. 2009, 50: 7121 13 The final product 5 appears to be unstable upon storing at room temperature. Zusatzmaterial Zusatzmaterial Supporting Information
