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:	Creators Email Pitt Username ORCID Gabarda, AE Du, W Isarno, T Tangirala, RS Curran, DP curran@pitt.edu CURRAN
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-dev.library.pitt.edu/id/eprint/20486

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