90414-70-3Relevant academic research and scientific papers
Asymmetric synthesis and in vivo biological inactivity of the right-hand terpenoid fragment of terpendole e
Oikawa, Masato,Hashimoto, Ryo,Sasaki, Makoto
supporting information; experimental part, p. 538 - 546 (2011/04/17)
Synthesis of the DEF-ring terpenoid fragment of terpendole E, an Eg5 inhibitor, is described. The DE-ring was constructed by a modification of Barrero's radical cyclization. The F-ring tetrahydropyran was then constructed by acid-induced cyclization of an epoxy alcohol, which was prepared by cross-metathesis followed by Shi's epoxidation. Cell-based assays indicated that the DEF-ring fragment is not capable of inhibiting cell growth and cell cycle progression of human cancer cell lines, indicating that the DEF-ring fragment alone is not sufficient for the biological activity. The DEF-ring terpenoid fragment of terpendole E, has been synthesized in 15 steps starting from farnesyl acetate, employing radical cyclization (DE-ring formation) and stereoselective cyclization of an epoxyalcohol (F-ring formation). Cell-based assays showed that the right-hand DEF-ring fragment is inactive in cell growth and cell cycle progression of human cancer cell lines.
Noxious-insect repellent
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, (2008/06/13)
PCT No. PCT/JP94/00885 Sec. 371 Date Nov. 6, 1996 Sec. 102(e) Date Nov. 6, 1996 PCT Filed Jun. 1, 1994Disclosed is a method of repelling noxious insects comprising the step of exposing said noxious insects to a composition containing from 0.1 to 90 wt. %, based on the total weight of the composition, of at least one of 2-(1-hydroxyalkyl)-cycloalkanols represented by the following formulae (2), (7) and (8): wherein R3 and R4 are independently a straight-chain or branched, saturated or unsaturated, hydrocarbon radical having 1-8 carbon atoms.
First general method for direct formylation of kinetically-generated ketone enolates
Zayia, Gregory H.
, p. 989 - 991 (2008/02/09)
(matrix presented) 2,2,2-Trifluoroethyl formate reacts rapidly at -78°C with preformed ketone enolates to give α-formyl ketones in good yields. In addition, this procedure allows for complete reversal of the regioselectivity of the classical Claisen react
Designed Chiral Acyl Radical Equivalents. Preparation and Cyclizations of Disymmetrically Substituted 1,3-Dioxabicyclo[4.4.0]decan-2-yl Radicals
Stien,Samy,Nouguier,Crich,Bertrand
, p. 275 - 286 (2007/10/03)
The diastereoselectivity of 5-exo-trigonal cyclizations of 2-(4-penten-1-yl)-1,3-dioxolan-2-yl and 2-(4- penten-1-yl)-1,3-dioxan-2-yl radicals is investigated. When dioxolanes or dioxanes derived from C2 symmetrically substituted diols are employed the diastereoselectivity is poor. In the dioxanyl series this is a consequence of the cyclization occurring through a twist-boat conformer. Disymmetrically substituted dioxanyl radicals, derived from the alcohols 21 and 41, are, however, constrained to chairlike conformations and accordingly give rise to highly diastereoselective cyclizations. Conditions are described for the hydrolysis of the resulting spiroacetals and for determination of the ee of the resulting 2-methylcyclopentanones.
Ultrasound-Promoted Cycloadditions in the Synthesis of Salvia miltiorrhiza Abietanoid o-Quinones
Lee, Junning,Snyder, John K.
, p. 4995 - 5008 (2007/10/02)
The ultrasound-promoted Diels-Alder reaction of 3-methyl-4,5-benzofurandione with appropriately substituted vinylcyclohexenes has led to the synthesis of tanshinone IIA, nortanshinone, tanshindiol B, methyl tanshinonate, and tanshinone IIB, biologically active metabolites of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge.Methyltanshinquinone, the dihydro derivative of the natural product, methylenetanshinquinone, was similarly prepared.The effect of ultrasound in promoting the cycloadditions parallels that of high pressure and improved the regioselectivity in favour of the natural isomers.
STEREOCHEMICAL VARIATIONS IN AQUEOUS CYCLOADDITIONS USING GLYCO-ORGANIC SUBSTRATES AS A CONSEQUENCE OF CHEMICAL MANIPULATIONS ON THE SUGAR MOIETY
Lubineau, Andre,Queneau, Yves
, p. 6697 - 6712 (2007/10/02)
Chemical modifications of the sugar moiety in dienyl glycosides allowed us to rationalize the stereochemistry of our aqueous cycloadditions using glyco-organic substrates.In this way, several dienyl glucosides having benzyl group in 2 or 6 position of the
Stereoelectronic Effects in the Conformation and Hydrolysis of Epimeric(4aα, 8aβ)-Hexahydrobenzo-2-(p-Nitrophenoxy)-2-Oxo-1,3,2λ5-Dioxaphosphorinanes and 4aα-methyl-8aβ-Pentahydrobenzo-2-(p-Nitrophenoxy)-2-Oxo-1,3,2λ5-Dioxaphosphorin
Taira, Kazunari,Lai, Kofen,Gorenstein, David G.
, p. 229 - 238 (2007/10/02)
The epimeric (4aα, 8aβ)-hexahydrobenzo-2-(p-nitrophenoxy)-2-oxo-1,3,2λ5-dioxaphosphorinanes 1a,1b (axial and pseudo-equatorial p-nitrophenoxy group) and 4aα-methyl-8aβ-pentahydrobenzo-2-(p-nitrophenoxy)-2-oxo-1,3,2λ5-dioxaphosphorina
GLYCO-ORGANIC SUBSTRATES IN ORGANIC SYNTHESIS. PREPARATION OF A WATER SOLUBLE BUTADIENYL-ETHER AND ITS USE IN AQUEOUS CYCLOADDITION.
Lubineau, Andre,Queneau, Yves
, p. 2653 - 2654 (2007/10/02)
A chiral water-soluble butadienyl-ether containing free glucose as hydrophilic moiety was synthesized and used in aqueous cycloaddition reaction with methacrolein to afford through pure endo transition state, only two diastereoisomers from which the sugar
