Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York Synthesis of a C-9 to C-18 Building Block of the Phenalamides Reinhard W. Hoffmann*, Eckart Haeberlin, Thorsten RohdeFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, GermanyFax: +49(6421)2828917; e-Mail: rwho@chemie.uni-marburg.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract In the context of a synthesis of phenalamide A2, the C-9 to C-18 building block 6 was synthesized. The stereogenic centers were generated by alkylation of an Evans oxazolidinone 12 and by a crotylboration reaction using the enantiomerically pure (E)-α-chlorocrotylboronate (4). Key words allylboration reaction - diastereoselectivity - natural products - stereoselective synthesis Volltext Referenzen References 1 Andrus MB. Lepore SD. J. Am. Chem. Soc. 1997, 119: 2327 2 Andrus MB. Lepore SD. Sclafani JA. Tetrahedron Lett. 1997, 38: 4043 3 Andrus MB. Turner TM. Asgari D. Li W. J. Org. Chem. 1999, 64: 2978 4 Mapp AK. Heathcock CH. J. Org. Chem. 1999, 64: 23 5 Hoffmann RW. Rohde T. Haeberlin E. Schäfer F. Org. Lett. 1999, 1: 1713 6 Andrus MB. Lepore SD. Turner TM. J. Am. Chem. Soc. 1997, 119: 12159 7a Namy J.-L. Boireau G. Abenhaim D. Bull. Soc. Chim. Fr. 1971, 3191 7b Anastasis P. Freer I. Overton KH. Picken D. Rycroft DS. Singh SB. J. Chem. Soc., Perkin Trans. 1 1987, 2427 8 Manusco AJ. Huang S.-L. Swern D. J. Org. Chem. 1978, 43: 2480 9 Wittig G. Reiff H. Angew. Chem. 1968, 80: 8 ; Angew. Chem., Int. Ed. Engl. 1968, 7, 7 10 Corey EJ. Enders D. Bock MG. Tetrahedron Lett. 1976, 7 11 Charette AB. Naud J. Tetrahedron Lett. 1998, 39: 7259 12 Evans DA. Ennis MD. Mathre DJ. J. Am. Chem. Soc. 1982, 104: 1737 13 Brown HC. Bhat KS. Randad RS. J. Org. Chem 1987, 52: 3701 14 Hoffmann RW. Dresely S. Lanz JW. Chem. Ber. 1988, 121: 1501 15 Hoffmann RW. Dresely S. Hildebrandt B. Chem. Ber. 1988, 121: 2225 16 Hoffmann RW. Dahmann G. Andersen MW. Synthesis 1994, 629 17 Hoffmann RW. Schäfer F. Haeberlin E. Rohde T. Körber K. Synthesis 2000, 2060 18 Cromwell NH. Creger PL. Cook KE. J. Am. Chem. Soc. 1956, 78: 4412