- Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants
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Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy-and tetramethoxybenzoic acids accessed by lithiation-carboxylation reactions. Direct enolate acylation was preferred over Baker-Venkataraman rearrangement when there were methoxy groups at both the 2-and the 6-position of the benzoic acid derivatives.
- Caldwell, Stuart T.,McPhail, Donald B.,Duthie, Garry G.,Hartley, Richard C.
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scheme or table
p. 23 - 33
(2012/03/07)
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- Synthesis of (±)- and (+)-perovskone
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A biomimetic synthesis of the triterpene (±)-perovskone was achieved featuring a remarkable polycyclization process in which three rings, four bonds, and five stereocenters were created in a single operation in 82% yield. This convergent synthesis required 16 steps, starting from vanillin, and proceeded in 9% overall yield. A second route to prepare optically active quinone 2 took 15 steps in 36% overall yield and featured a palladium-catalyzed reductive allylic transposition to establish the C-5 chirality stereospecifically. Quinone (-)-2 was converted to (+)-perovskone (1) via a polycyclization cascade, which created four rings, five bonds, and six stereocenters in a single operation in 50% yield.
- Majetich, George,Zhang, Yong,Tian, Xinrong,Britton, Jonathan E.,Li, Yang,Phillips, Ryan
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experimental part
p. 10129 - 10146
(2012/02/03)
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- Ga(IIl)-catalyzed cycloisomerization approach to (±)-icetexone and (±)-epi-icetexone
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"Chemical eqation presented" A Ga(III)-catalyzed cycloisomerization reaction provides expedient access to a benzannulated cycloheptadiene bearing a cyano group, which has been applied to the syntheses of several icetexane diterpenoids including icetexone
- De Jesus Cortez, Felipe,Sarpong, Richmond
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supporting information; experimental part
p. 1428 - 1431
(2010/07/03)
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- A concise and efficient synthesis of protected actinoidic acid, the degradation product of vancomycin
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Protected actinoidic acid 2, one of the degradation products of vancomycin, has been efficiently synthesized by a convergent route which is amenable to large scale application as well as to asymmetric synthesis.
- Zhu, Jieping,Beugelmans, Rene,Bigot, Antony,Singh, Girij Pal,Bois-Choussy, Michele
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p. 7401 - 7404
(2007/10/02)
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- THE SYNTHESIS OF DESERTORIN C, A BICOUMARIN FROM THE FUNGUS EMERICELLA DESERTORUM
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The structure of desertorin C, a metabolite of the mould Emericella desertorum, is confirmed as 4,4',7,7'-tetramethoxy-5,5'-dimethyl-6,8'-bicoumarin (6), by its synthesis in racemic form.The key step involved the construction of the unsymmetrical biphenyl
- Rizzacase, Mark A.,Sargent, Melvyn V.
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p. 2425 - 2428
(2007/10/02)
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