Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach

• Jingjing Wang,
• Samuel Z. Y. Ting and
• Joanne E. Harvey

Beilstein J. Org. Chem. 2015, 11, 1815–1822, doi:10.3762/bjoc.11.197

• Jingjing Wang Samuel Z. Y. Ting Joanne E. Harvey Centre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand 10.3762/bjoc.11.197 Abstract Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical

• products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment. Keywords: Bestmann ylide; dactylolide; dienoate; (triphenylphosphoranylidene)ketene; zampanolide; Introduction (Triphenylphosphoranylidene)ketene, Ph3P=C=C=O (1), was

• -component reaction between (triphenylphosphoranylidene)ketene (Bestmann ylide, 1), an alcohol and an unsaturated aldehyde delivers α,β,γ,δ-unsaturated esters. This methodology enabled the facile synthesis of E,Z-dienoate products 5b and 5c, which represent two-thirds of the dactylolide/zampanolide