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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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1365-3075
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Volume 85, Issue 6 (May 2013)

Issues

Total synthesis of (+)-spirastrellolide A methyl ester: Challenges and discoveries

Ian Paterson / Philip Maltas / Edward A. Anderson
Published Online: 2013-05-20 | DOI: https://doi.org/10.1351/PAC-CON-13-01-01

This review focuses on recent synthetic efforts by our group towards spirastrellolide A methyl ester, a complex marine macrolide containing two spiroacetal ring systems that shows promising anticancer properties. The evolution of a flexible, modular strategy leading to the first total synthesis of (+)-spirastrellolide A methyl ester, and the associated challenges overcome, are highlighted, particularly in dealing with the initial structural ambiguities. This work enabled the development of an improved second-generation synthesis, which revealed a critical dependence of the key macrolactonization step on the nature of the protecting groups in the linker region between the spiroacetal motifs.

Keywords: anticancer drugs; macrolides; natural products; protein phosphatases; stereocontrolled synthesis

Conference

International Conference on Organic Synthesis (ICOS-19), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 19th, Melbourne, Australia, 2012-07-01–2012-07-06

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About the article

Published Online: 2013-05-20

Published in Print: 2013-05-20


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-13-01-01.

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