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

Gabarda, AE and Du, W and Isarno, T and Tangirala, RS and Curran, DP (2002) Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans. Tetrahedron, 58 (32). 6329 - 6341. ISSN 0040-4020

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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 to this important new class of antitumor agents. © 2002 Published by Elsevier Science Ltd.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Gabarda, AE
Du, W
Isarno, T
Tangirala, RS
Curran, DPcurran@pitt.eduCURRAN
Date: 5 August 2002
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 58
Number: 32
Page Range: 6329 - 6341
DOI or Unique Handle: 10.1016/s0040-4020(02)00632-4
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 07 Feb 2014 00:02
Last Modified: 29 Jan 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/20486

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