A New Stereocontrolled Synthesis of Dihydroxerulin, a Potent Noncytotoxic Inhibitor of the Biosynthesis of Cholesterol

✍ Scribed by Renzo Rossi; Fabio Bellina; Antonella Catanese; Luisa Mannina; Daniela Valensin

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 263 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)01030-3

✦ Synopsis

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]-5H-furan-2-one, 15, and the phosphonium ylid which derived from [(E)-2-decen-4,6-diyn-1yl]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-[(2E)-4-hydroxy-2-butenylidene]-5H-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.