Concepedia

Towards the combinatorial synthesis of spongistatin fragment libraries by using asymmetric aldol reactions on solid support

Ian Paterson, Dirk Gottschling, Dirk Menche

Chemical Communications · 2005 · 32 citations · 22 references

DOI

Concepts

Abstract

By relying on asymmetric boron-mediated aldol reactions, solid phase methodology for the stereoselective synthesis of highly substituted spiroacetals was developed and applied to the preparation of a complex AB-spiroacetal subunit of the antimitotic agent spongistatin 1 (altohyrtin A).

References

22

Antineoplastic agents. 257. Isolation and structure of spongistatin 1

George R. Pettit, Zbigniew A. Chicacz, Feng Gao et al. · The Journal of Organic Chemistry · 1993 · 259 citations

, , +19

Altohyrtin A, a potent anti-tumor macrolide from the Okinawan marine sponge Hyrtios altum

Motomasa Kobayashi, Shunji Aoki, Haruhiko Sakai et al. · Tetrahedron Letters · 1993 · 146 citations

, , +4

Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Fragment Assembly and Revision of the Spongistatin 2 Stereochemical Assignment

David A. Evans, B. Wesley Trotter, Bernard Côté et al. · Angewandte Chemie International Edition in English · 1997 · 127 citations

, , +18

Stereocontrolled Total Synthesis of (+)-Altohyrtin A/Spongistatin 1 Financial support was provided by the EPSRC (GR/L41646), Cambridge Commonwealth Trust (Scholarship to M.J.C.), EC (Marie Curie Postdoctoral Fellowship to J.L.A.), DFG (Postdoctoral Fellowship to T.T.), NSERC-Canada (Postdoctoral Fellowship to R.M.O.), Churchill College (Research Fellowship to D.J.W.), Kingapos;s College and Sims Fund, Cambridge (Scholarship to D.Y.K.C.). We also thank Merck and AstraZeneca Pharmaceuticals for generous support, and Dr. Anne Butlin (AZ) and Dr. Nick Bampos (Cambridge) for valuable assistance.

Ian Paterson, David Y.‐K. Chen, Mark J. Coster et al. · Angewandte Chemie International Edition · 2001 · 116 citations

The Spongistatins: Architecturally Complex Natural Products-Part Two: Synthesis of the C(29-51) Subunit, Fragment Assembly, and Final Elaboration to (+)-Spongistatin 2

Amos B. Smith, Qiyan Lin, Victoria A. Doughty et al. · Angewandte Chemie International Edition · 2001 · 108 citations