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 Bestmannylide [(triphenylphosphoranylidene)ketene] acts as a chemical
linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achieved through the coupling of Bestmannylide, an alcohol and an α,β-unsaturated
products zampanolide and dactylolide is investigated using Bestmannylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment.
Keywords: Bestmannylide; dactylolide; dienoate; (triphenylphosphoranylidene)ketene; zampanolide; Introduction
(Triphenylphosphoranylidene)ketene, Ph3P=C=C=O (1), was
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Graphical Abstract
Figure 1:
Structures of (−)-zampanolide (2) and (+)-dactylolide (3).