97232-74-1Relevant academic research and scientific papers
Inhibition of Vertebrate Squalene Epoxidase by Extended and Truncated Analogues of Trisnorsqualene Alcohol
Sen, Stephanie E.,Wawrzenczyk, Czeslaw,Prestwich, Glenn D.
, p. 1698 - 1701 (1990)
The epoxidation of squalene to (3S)-2,3-epoxysqualene and subsequent cyclization to lanosterol are keys steps in vertebrate cholesterol biosynthesis.Trisnorsqualene alcohol (TNSA) has previously been reported as a potent inhibitor of vertebrate squalene epoxidase, with IC50 = 4 μM for pig liver (J.Am.Chem.Soc. 1989, 111, 1508-1510).Analogues with extended and truncated carbon skeletons have been prepared and tested for pig liver squalene epoxidase (SE) inhibition.Most of the structural analogues were poor inhibitors of vertebrate SE, with the exception of bisnorsqualene alcohol which had the same activity as TNSA.These results support the theory that an intact trisnorsqualene moiety is required for activity.
Zeolite NaY-promoted monocyclization of epoxy polyene terpenes: A unique route for the direct synthesis of incompletely cyclized naturally occurring terpenols
Tsangarakis, Constantinos,Raptis, Christos,Arkoudis, Elias,Stratakis, Manolis
body text, p. 1587 - 1600 (2009/07/30)
A variety of epoxy polyene terpenes cyclize readily by confinement within zeolite NaY to form primarily products of monocyclization. The monocyclization pathway is highly predominant, irrespectively of the side chain of the epoxy terpene, while the monocyclic products possess regioselectively an exomethylenic double bond. The selective monocyclization in the case of epoxyfarnesyl acetate, epoxyfarnesylacetone or 2,3-epoxysqualene, provides a direct route to the synthesis of a variety of natural products, such as elengasidiol, farnesiferols B-D, achilleol A, camelliol C and to four farnesylacetone-derived metabolites isolated from the brown algae Cystophora monoliformis. The optical rotation of achilleol A derived from the cyclization of (S)-2,3-epoxysqualene matches with that of the natural product, thus the absolute configuration of achilleol A was established as 1S,3R. From the mechanistic point of view, the NaY-promoted cyclization of 9,10-epoxygeranylacetone, selectively deuterium labelled at the C-10 methyl group, is >97% stereoselective with respect to the topicity of the gem-dimethyl group. This result is in agreement with a concerted mechanism. Finally, we have proved through labelling experiments, for the first time, that the biomimetic transformation of epoxy polyene terpenes to 2,3,4-trimethylcyclohexanones upon acid catalysis is a highly stereoselective process. Thus, the less hindered gem-methyl group on the epoxide functionality becomes α- to the carbonyl in the final isomerized product.
Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids: Facile syntheses of biologically active terpenoids
Barrero, Alejandro F.,Del Moral, Jose F. Quilez,Herrador, M. Mar,Cortes, Manuel,Arteaga, Pilar,Catalan, Julieta V.,Sanchez, Elena M.,Arteaga, Jesus F.
, p. 5811 - 5814 (2007/10/03)
Regioselective halogenation of the terminal isopropylidene unit of different acyclic polyolefinic polyprenoids (farnesyl acetate, geranylgeranyl acetate, squalene, etc.) using NCS/catalytic polymer-supported selenenyl bromide is described; good to excellent yields are obtained (68-96%). The first applications of this protocol include the concise synthesis of bioactive terpenoids 1-3.
SYNTHESIS OF E-C5-HOMOLOG OF SQUALENE
Veselovskii, A. B.,Filippova, T. M.,Moiseenkov, A. M.
, p. 2107 - 2110 (2007/10/02)
A stereospecific synthesis has been carried out for a monoisoprenolog of squalene by a cross-combination according to the Wurtz reaction of prenylmagnesium chloride with 3-hydroxyisosqualene tosylate.
