Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo-Symmetry

The challenging structure and potent growth inhibition properties against a variety of human cancer cell lines make Spongistatin 1 (1) an exciting target for total synthesis. Enantioselective total synthesis has been achieved by exploiting a latent element of pseudo‐symmetry (‐ ‐ ‐ ‐ ‐ =pseudo‐C2 ax...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-08, Vol.44 (34), p.5433-5438
Main Authors: Ball, Matthew, Gaunt, Matthew J., Hook, David F., Jessiman, Alan S., Kawahara, Shigeru, Orsini, Paolo, Scolaro, Alessandra, Talbot, Adam C., Tanner, Huw R., Yamanoi, Shigeo, Ley, Steven V.
Format: Article
Language:English
Subjects:
Biological Factors - chemical synthesis
Biological Factors - chemistry
dithianes
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
natural products
pseudo-symmetry
spongistatin 1
Stereoisomerism
total synthesis
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Summary:The challenging structure and potent growth inhibition properties against a variety of human cancer cell lines make Spongistatin 1 (1) an exciting target for total synthesis. Enantioselective total synthesis has been achieved by exploiting a latent element of pseudo‐symmetry (‐ ‐ ‐ ‐ ‐ =pseudo‐C2 axis) within the ABCD bis(spiroketal) fragment (red substructure).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502008