diastereoselective syntheses of new analogues of the farnesyltransferase inhibitor rpr 130401

1
2005 Fused pyrrole derivatives R 0160 Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhib- itor RPR 130401. — The synthesis of the title analogues (IX) and (X) is achieved via stereoselective cycloaddition of the pyrroline (III) to the benzofuran (IV). Depending on the conditions, the syn- or the anti-adduct can be formed predominantly. Addition- ally, it is shown that the nature of the N-substituent also affects the stereoselectivity. Unfortunately, (IX) and (X) do not exhibit any farnesyltransferase inhibitory activity. — (PICHON, N.; MARRISON-MARCHAND, A.; MAILLIET, P.; MADDALUNO*, J.; J. Org. Chem. 69 (2004) 21, 7220-7227; Lab. Fonct. Azotees Oxygenees Complexes, Inst. Rech. Chim. Org. Fine, Univ. Rouen, F-76821 Mont-Saint-Aignan, Fr.; Eng.) — Jannicke 07- 105

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Page 1: Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401

2005

Fused pyrrole derivativesR 0160 Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhib-

itor RPR 130401. — The synthesis of the title analogues (IX) and (X) is achieved via stereoselective cycloaddition of the pyrroline (III) to the benzofuran (IV). Depending on the conditions, the syn- or the anti-adduct can be formed predominantly. Addition-ally, it is shown that the nature of the N-substituent also affects the stereoselectivity. Unfortunately, (IX) and (X) do not exhibit any farnesyltransferase inhibitory activity. — (PICHON, N.; MARRISON-MARCHAND, A.; MAILLIET, P.; MADDALUNO*, J.; J. Org. Chem. 69 (2004) 21, 7220-7227; Lab. Fonct. Azotees Oxygenees Complexes, Inst. Rech. Chim. Org. Fine, Univ. Rouen, F-76821 Mont-Saint-Aignan, Fr.; Eng.) — Jannicke

07- 105