Tetrahedron letters

Diastereoselective addition of Grignard reagents to azetidine-2, 3-dione: Synthesis of novel Taxol® analogues

…, WS Schwartz, C Fairchild, Q Gao, S Huang, BH Long…

Index: Kant, Joydeep; Schwartz, Wendy S.; Fairchild, Craig; Gao, Qi; Huang, Stella; Long, Byron H.; Kadow, John F.; Langley, David R.; Farina, Vittorio; Vyas, Dolatrai Tetrahedron Letters, 1996 , vol. 37, # 36 p. 6495 - 6498

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Citation Number: 65

Abstract

Synthesis and cytotoxicity properties of novel C-2′ analogues of paclitaxel are described. The analogues were synthesized using Holton's β-lactam approach to append the side chain on baccatin III. The key intermediate to the synthesis of novel analogues was prepared employing an unprecedented stereocontrolled addition of Grignard reagent to a chiral azetidine-2, 3-dione.