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

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

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...

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Bibliographic Details
Published in:Tetrahedron Vol. 58; no. 32; pp. 6329 - 6341
Main Authors: Gabarda, Ana E, Du, Wu, Isarno, Thomas, Tangirala, Raghuram S, Curran, Dennis P
Format: Journal Article
Language:English
Published: Elsevier Ltd 05-08-2002
Subjects:
antitumor
homosilatecans
topoisomerase
antitumor
homosilatecans
topoisomerase
Online Access:Get full text
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Summary: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 to this important new class of antitumor agents. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00632-4