Synthesis of the C1–C17 fragment of the archazolids by complex cis-homodimer cross metathesis

• DOI: 10.1016/j.tetlet.2015.05.014
• Publication Date: 2015-05-11T17:16:53Z
• Authors: Steven M. Swick; Sara L. Schaefer; Gregory W. O’Neil
• Keywords: Salt metathesis reaction; Ring-Closing Metathesis; Ring-opening metathesis polymerisation; Fragment (logic)

A synthesis of the C1-C17 fragment of the archazolids is described featuring a complex cross-metathesis coupling reaction between a cis-homodimer (prepared by silyl-tethered ring-closing metathesis) and the Z,Z-terminal triene containing "eastern domain" of the archazolid natural products. This cross-metathesis was only successful when using the cis- as opposed to the monomer or trans-homodimer, with the cis-dimer added batchwise to minimize cis/trans-isomerization. The product was obtained in an optimized 78% yield using the Hoveyda-Grubbs catalyst at 50 °C in toluene.