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Pure and Applied Chemistry

The Scientific Journal of IUPAC

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

12 Issues per year


IMPACT FACTOR 2016: 2.626
5-year IMPACT FACTOR: 3.210

CiteScore 2016: 2.45

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Source Normalized Impact per Paper (SNIP) 2016: 1.049

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ISSN
1365-3075
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Volume 79, Issue 4 (Jan 2007)

Issues

Progress toward a total synthesis of spirastrellolide A

Ian Paterson / Edward A. Anderson / Stephen M. Dalby / Jong Ho Lim / Olivier Loiseleur / Philip Maltas / Christian Moessner
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200779040667

Progress toward a total synthesis of spirastrellolide A, a 38-membered marine macrolide, is reported. Syntheses of two diastereomers of the C1-C25 region, and an evolving Sharpless dihydroxylation strategy toward a C26-C40 fragment, are described. The syntheses exploit boron-mediated aldol chemistry to install key stereocenters, and feature late-stage thermodynamically controlled spiroacetalizations.

Keywords: aldol; anticancer; macrolides; natural products; spiroacetal; stereocontrolled synthesis

Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28

References

About the article

Published Online: 2009-01-01

Published in Print: 2007-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200779040667.

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