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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
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ISSN
1365-3075
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Volume 80, Issue 8 (Jan 2008)

Issues

Total synthesis of cytotoxic marine macrolides: Callipeltoside A, aurisides A and B, and dolastatin 19

Ian Paterson / Alison D. Findlay
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200880081773

Synthetic studies pertaining to a novel class of structurally related glycosidic 14-membered macrolides of marine origin are reported. The evolution of a versatile aldol-based strategy that culminated in the total syntheses of callipeltoside A and aurisides A and B is detailed. Using a combination of biogenetic considerations and conformational analysis, a revised stereochemical assignment for the related polyketide dolastatin 19 was proposed and validated by total synthesis.

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

Conference

CHEM-BIO-TECH-2007, a joint meeting of the IUPAC 1st Symposium on Chemical Biotechnology (ISCB-1) and the 8th Symposium on Bioorganic Chemistry (ISBOC-8), International Symposium on Bioorganic Chemistry, ISBOC, Bioorganic Chemistry, Turin, Italy, 2007-08-08–2007-08-11

References

About the article

Published Online: 2009-01-01

Published in Print: 2008-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200880081773.

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