Abstract
Abstract Dihydroxerulin, 1 , has been stereoselectively synthesized by a convergent approach in which a key step was the Wittig reaction between ( Z )-5-[( E )-3-formyl-2-propenylidene]-5 H -furan-2-one, 15 , and the phosphonium ylid which derived from [( E )-2-decen-4,6-diyn-1-yl]triphenylphosphonium bromide, 19 . Compound 19 was conveniently prepared by a short reaction sequence involving a Stille reaction between 1-trimethylstannyl-1,3-heptadiyne, 17 , and ( E )-3-iodo-2-propen-1-ol, 18 . On the other hand, compound 15 was prepared in eight steps by a reaction sequence in which an immediate precursor to this butenolide, i.e. ( Z )-5-[(2 E )-4-hydroxy-2-butenylidene]-5 H -furan-2-one, 34 , was regio- and stereoselectively synthesized by Ag(I)-catalysed lactonization of the corresponding ( Z )-2-en-4-ynoic acid. The structure and stereochemistry of 1 were established on the basis of its 1 H and 13 C NMR spectra at 600 and 150 MHz, respectively, and by a combination of 2D NMR techniques.
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