Total Synthesis of Halichondrin C

Akihiko Yamamoto , Atsushi Ueda , Paul Brémond (1) , Paolo S. Tiseni , Yoshito Kishi

1 ICR - Institut de Chimie Radicalaire

The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.

Domains: Chemical Sciences

Akihiko Yamamoto, Atsushi Ueda, Paul Brémond, Paolo S. Tiseni, Yoshito Kishi. Total Synthesis of Halichondrin C. Journal of the American Chemical Society, 2012, 134 (2), pp.893--896. ⟨10.1021/ja2108307⟩. ⟨hal-01460423⟩