title: Synthesis of the C1-C17fragment of the archazolids by complexcis-homodimer cross metathesis.
abstract: A synthesis of the C1-C17fragment of the archazolids is described featuring a complex cross-metathesis coupling reaction between acis-homodimer (prepared by silyl-tethered ring-closing metathesis) and theZ,Z-terminal triene containing "eastern domain" of the archazolid natural products. This cross-metathesis was only successful when using thecis- as opposed to the monomer ortrans-homodimer, with thecis-dimer added batchwise to minimizecis/trans-isomerization. The product was obtained in an optimized 78% yield using the Hoveyda-Grubbs catalyst at 50 °C in toluene.
authors.affiliation: Department of Chemistry, Western Washington University, Bellingham, WA, 98225, USA.
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swick
authors.affiliation: Department of Chemistry, Western Washington University, Bellingham, WA, 98225, USA.
authors.forename: Sara L
authors.initials: SL
authors.lastname: Schaefer
authors.affiliation: Department of Chemistry, Western Washington University, Bellingham, WA, 98225, USA.
authors.forename: Gregory W
authors.initials: GW
authors.lastname: O'Neil
keywords: VATPase inhibitor; cis-homodimer; cross metathesis; homodimerization; silyl-tethered ring closing metathesis