Tetrahedron

Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

AE Gabarda, W Du, T Isarno, RS Tangirala, DP Curran

Index: Gabarda, Ana E; Du, Wu; Isarno, Thomas; Tangirala, Raghuram S; Curran, Dennis P Tetrahedron, 2002 , vol. 58, # 32 p. 6329 - 6341

Full Text: HTML

Citation Number: 28

Abstract

An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry ...