91060-73-0Relevant academic research and scientific papers
Total synthesis of polyene natural product dihydroxerulin by mild organocatalyzed dehydrogenation of alcohols
Xie, Hexin,Zhang, Shilei,Li, Hao,Zhang, Xinshuai,Zhao, Sihan,Xu, Zian,Song, Xixi,Yu, Xinhong,Wang, Wei
supporting information; experimental part, p. 2230 - 2234 (2012/03/27)
Polyene synthesis: An efficient approach to the total synthesis of polyene natural product dihydroxrulin (1) is described. A novel, mild, direct organocatalytic IBX-mediated dehydrogenation process of simple alcohols to enals has been developed, which serves as a key step in the synthesis (see scheme). Copyright
A new stereocontrolled synthesis of dihydroxerulin, a potent noncytotoxic inhibitor of the biosynthesis of cholesterol
Rossi, Renzo,Bellina, Fabio,Catanese, Antonella,Mannina, Luisa,Valensin, Daniela
, p. 479 - 487 (2007/10/03)
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-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-[(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 1H and 13C NMR spectra at 600 and 150 MHz, respectively, and by a combination of 2D NMR techniques. (C) 2000 Elsevier Science Ltd.
