Dihydroxerulin 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, and the phosphonium ylid which derived from [(E)-2-decen-4,6-diyn-1-yl]triphenylphosphonium bromide. This compound 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. 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, 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 1H and 13C NMR spectra at 600 and 150 MHz, respectively, and by a combination of 2D NMR techniques
A new stereocontrolled synthesis of dihydroxerulin, a potent noncytotoxic inhibitor of the biosynthesis of cholesterol / Renzo, Rossi; Fabio, Bellina; Antonella, Catanese; Mannina, Luisa; Daniela, Valensin. - In: TETRAHEDRON. - ISSN 0040-4020. - ELETTRONICO. - 56:3(2000), pp. 479-487. [10.1016/s0040-4020(99)01030-3]
A new stereocontrolled synthesis of dihydroxerulin, a potent noncytotoxic inhibitor of the biosynthesis of cholesterol
MANNINA, LUISA;
2000
Abstract
Dihydroxerulin 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, and the phosphonium ylid which derived from [(E)-2-decen-4,6-diyn-1-yl]triphenylphosphonium bromide. This compound 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. 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, 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 1H and 13C NMR spectra at 600 and 150 MHz, respectively, and by a combination of 2D NMR techniquesI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
