104265-73-8Relevant academic research and scientific papers
Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings: a convergent synthesis of diverse benzofuran neolignans.
Akai,Morita,Iio,Nakamura,Kita
, p. 2279 - 2282 (2000)
A convergent synthesis of diversely substituted benzofuran neolignans (8) is described employing a single p-sulfinyl group on the phenols (3) as an ambident functional group for two types of carbon-carbon bond-forming reactions: (i) the direct synthesis of the dihydrobenzofuran skeletons through an aromatic Pummerer-type reaction and (ii) the ipso-substitution of the sulfur functional group by carbon substituents through a ligand exchange reaction.
Biomimetic synthesis of the neolignans kadsurenone, denudatin B, O- methyl-liliflodione, and liliflol B
Horne, David A.,Yakushijin, Kenichi,Buechi, George
, p. 5443 - 5447 (2007/10/03)
Synthesis of (±)-kadsurenone (1), (±)-denudatin B (2), (±)-O-methyl- liliflodione (3a), and (±)-liliflol B (14) is described. The key synthetic step is a biomimetic cationic cycloaddition between E- or Z-1,2-dimethoxy-4- propenylbenzene (11) and ortho-qui
Stereospecific Lewis Acid-Promoted Reactions of Styrenyl Systems with 2-Alkoxy-(6-alkyl)-1,4-benzoquinones: Scope, Limitations, and Synthetic Applications
Engler, Thomas A.,Combrink, Keith D.,Letavic, Michael A.,Lynch, Kenneth O.,Ray, James E.
, p. 6567 - 6587 (2007/10/02)
Titanium(IV)-promoted reactions of various (E)-1-propenylbenzenes with 2-methoxy- and 2-methoxy-6-methyl-1,4-benzoquinones produce trans 2-aryl-6-methoxy-3-(and 4-di)methyl-2,3-dihydro-5-benzofuranols (10-12), rel-(1S,6R,7R,8R)-3-methoxy-8-aryl-7-(and 1-di)methylbicyclooct-3-ene-2,5-diones (2 + 2 cycloadducts, 13-15) and/or rel-(1R,5R,6R,7R)-7-aryl-3-hydroxy-6-(and 4)-methylbicyclooct-3-ene-2,8-diones (5 + 2 cycloadducts, 16/17).In many cases, each of the three products can be obtained selectively in good yield by control of reaction conditions and/or by choice of substituents on the quinone or the propenylbenzene.The dihydrobenzofurans are formed stereoselectively, whereas the formation of the bicyclo systems are stereospecific processes.Thus, reactions of (Z)-1-propenylbenzenes afford rel-(1R,6S,7R,8R)-8-aryl-3-methoxy-7-methylbicyclooct-3-ene-2,5-diones (24, 25).No bicyclosystems are found in reactions of the (Z)-propenylbenzenes.The products all apparently result from a thermally allowed 2? + 4? (2 + 5) cycloaddition of the propenylbenzene with a 2-methoxy-4-oxo-2,5-cyclohexadienyl carbocation intermediate (26) formed by coordination of the Ti(IV) to the C-1 carbonyl oxygen of the quinone.In the cycloaddition, the aryl ring of the propenylbenzene occupies an endo position with respect to the pentadienyl carbocation moiety of 26 and the bicyclo carbocation product of the cycloaddition (28/29) either undergoes dealkylation or rearrangement to yield the observed products.Treatment of the bicylo systems with protic acid effects their rearrangement to the dihydrobenzofuranols.Reactions of 2-propenylbenzenes and arylcycloalkenes with the quinones regioselectively give dihydrobenzofuranols 43-45 and 49-54, respectively; a 2 + 2 cycloadduct is found in low yield in only one case.The 7-aryl-3-hydroxy-6-methylbicyclooct-3-ene-2,8-diones are produced exclusively in reactions of 2-((4-methoxybenzyl)oxy)-1,4-benzoquinones with various propenylbenzenes.Application of these reactions to the synthesis of (+/-)-obtusafuran, (+/-)-liliflol-B, (+/-)-kadsurenone, and (+/-) denudatin are reported.
Mechanistic Aspects and Synthetic Applications of the Electrochemical and Iodobenzene Bis(trifluoroacetate) Oxidative 1,3-Cycloadditions of Phenols and Electron-Rich Styrene Derivatives
Gates, Bradley D.,Dalidowicz, Peter,Tebben, Andrew,Wang, Shaopeng,Swenton, John S.
, p. 2135 - 2143 (2007/10/02)
Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative.The yield o
A Convergent Route to Dihydrobenzofuran Neolignans via a Formal 1,3-Cycloaddition to Oxidized Phenols
Wang, Shaopeng,Gates, Bradley D.,Swenton, John S.
, p. 1979 - 1981 (2007/10/02)
Oxidation of p-methoxy-substituted phenols with iodobenzene bis-trifluoroacetate in the presence of electron-rich styrene derivatives affords trans-dihydrobenzofurans stereoselectively.
Structure-Activity Relationships of Kadsurenone Analogues
Ponpipom, Mitree M.,Bugianesi, Robert L.,Brooker, David R.,Yue, Bao-Zhen,Hwang, San-Bao,Shen, Tsung-Ying
, p. 136 - 142 (2007/10/02)
Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol.Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 * 10-7 M, which is about 50percent of the activity of the natural product (IC50 = 1 * 10-7 M).The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.
TOTAL SYNTHESIS OF KADSURENONE AND ITS ANALOGS
Ponpipom, M. M.,Yue, B. Z.,Bugianesi, R. L.,Brooker, D. R.,Chang, M. N.,Shen, T. Y.
, p. 309 - 312 (2007/10/02)
Kadsurenone, a specific receptor antagonist of platelet-activating factor and a natural product isolated from Piper futokadsura was prepared in three steps from 3,4-dimethoxycinnamyl alcohol and allyloxyphenol via rac-(2S,3S)-5-allyl-6-hydroxy-2-(3,4-dime
