Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo-Symmetry (pages 5433–5438)
Matthew Ball, Matthew J. Gaunt, David F. Hook, Alan S. Jessiman, Shigeru Kawahara, Paolo Orsini, Alessandra Scolaro, Adam C. Talbot, Huw R. Tanner, Shigeo Yamanoi and Steven V. Ley
Article first published online: 1 AUG 2005 | DOI: 10.1002/anie.200502008
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).