Synthesis of amphidinolide Y precursors |
| |
Authors: | Laura Mola,Anna OlivellaFè lix Urpí ,Jaume Vilarrasa |
| |
Affiliation: | Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Diagonal 645, 08028 Barcelona, Catalonia, Spain |
| |
Abstract: | The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-1-ol, which gave the C3–C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1–C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H–G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H–G-II Ru complex were required for complete conversion. |
| |
Keywords: | Formal total synthesis Amphidinolides Ring-closing metathesis (RCM) Macrocyclizations |
本文献已被 ScienceDirect 等数据库收录! |
|