71135-95-0Relevant articles and documents
Total synthesis of (+/-)-dihydrospiniferin-1 via a polyfluoro alkanosulfonyl fluoride induced tandem carbonium ion rearrangement reaction.
Chen, Ling,Ding, Kai,Tian, Wei-Sheng
, p. 838 - 839 (2003)
A novel polyfluoroalkanosulfonyl fluoride induced carbonium ion rearrangement reaction of gamma-hydroxymethyl cyclohexenone has been used for the total synthesis of (+/-)dihydrospiniferin 1.
[2.2.2]- to [3.2.1]-Bicycle Skeletal Rearrangement Approach to the Gibberellin Family of Natural Products
Smith, Brandon R.,Njardarson, Jon T.
, p. 2993 - 2996 (2018/05/28)
Synthetic studies toward the gibberellin family of natural products are reported. An oxidative dearomatization/Diels-Alder cascade assembles the carbon skeleton as a [2.2.2]-bicycle, which is then transformed to the [3.2.1]-bicyclic gibberellin core via a
CYCLOHEXEN-1-YL-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS
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, (2016/02/28)
The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacolo
Total synthesis of (+/-)-frondosin B and (+/-)-5-epi-liphagal by using a concise (4+3) cycloaddition approach
Laplace, Duchan R.,Verbraeken, Bart,Van Hecke, Kristof,Winne, Johan M.
, p. 253 - 262 (2014/01/17)
A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl-type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven-membered rings. Cycloheptanes: Furfuryl alcohols serve as effective three-carbon dienophiles for a wide range of dienes in stereoselective cycloaddition reactions. This efficient reaction has been used to prepare two cycloheptanoid natural products, offering a conceptually straightforward and short synthetic entry into a biologically interesting class of polycyclic meroterpenoids (see scheme; TFA = trifluoroacetic acid). Copyright
Rapid methylation on carbon frameworks useful for the synthesis of 11CH3-incorporated PET tracers: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkene
Hosoya, Takamitsu,Sumi, Kengo,Doi, Hisashi,Wakao, Masahiro,Suzuki, Masaaki
, p. 410 - 415 (2007/10/03)
The Pd(0)-mediated rapid coupling of methyl iodide with an excess of alkenyltributylstannane was examined with the aim of incorporating a short-lived 11C-labeled methyl group into a biologically significant organic compound with a 1-methylalkene unit for the synthesis of a PET tracer. Four sets of reaction conditions (A-D) were used, all performed in DMF at 60 °C for 5 min. Condition B, using CH3I/stannane/Pd2(dba) 3/P(o-tolyl)3/CuCl/K2CO3 (1: 40: 0.5: 4-6: 2: 5), works well in almost all cases. Condition D, using CH 3I/stannane/Pd2(dba)3/P(o-tolyl) 3/CuX (X = Br, Cl, or I)/CsF (1: 40: 0.5-5: 2-20: 2-20: 5-50), shows the best results with regard to general applicability to tin substrates, affording the corresponding methylated product in >90% yield based on consumption of methyl iodide. P(t-Bu)2Me was less effective than P(o-tolyl)3, particularly for α,β-unsaturated carbonyl substrates. No regio- or stereoisomerization occurred under these reaction conditions. The efficiency of the protocol was demonstrated by synthesis of an 11C-methylated compound. The Royal Society of Chemistry 2006.
Efficient and reusable PdCl2(MeCN)2/CuCl 2/PEG-400 system for cyclization of alkenyl β-keto esters and amides
Li, Jin-Heng,Zhu, Qi-Ming,Liang, Yun,Yang, Dan
, p. 5347 - 5349 (2007/10/03)
PEG-400 [poly(ethylene glycol-400)] was found as an effective medium for the PdCl2(MeCN)2-catalyzed hydroalkylation cyclization of alkenyl β-keto esters and amides. In PEG-400, no additives such as Me 3SiCl and Ln(OTf)3 were required for the complete conversion of alkenyl β-keto esters. The results also snowed that CuCl 2 could promote the reaction. In the presence of PdCl 2(MeCN)2, CuCl2, and PEG-400, various alkenyl β-keto esters and amides underwent a selective cyclization reaction to give good to excellent yields of the desired six-membered-ring carbocycles. Furthermore, the PdCl2(MeCN)2/CuCl2/PEG-400 system could be recycled and reused five times without any loss of catalytic activity.
Lanthanide triflate-promoted palladium-catalyzed cyclization of alkenyl β-keto esters and amides
Yang, Dan,Li, Jin-Heng,Gao, Qiang,Yan, Yi-Long
, p. 2869 - 2871 (2007/10/03)
(Matrix presented) Lanthanide triflates were found to promote the palladium-catalyzed cyclization of alkenyl β-keto esters and amides. In the presence of catalytic amounts of PdCl2(MeCN)2 and Ln(OTf)3, various alkenyl β-keto esters and amides underwent regioselective cyclization reactions to give six-, seven-, or eight-membered-ring carbocycles in moderate to excellent yields.
Heterocyclic metalloprotease inhibitors
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, (2008/06/13)
The invention provides compounds of formula as described in the claims, or an optical isomer, diastereomer or enantiomer thereof, or a pharmaceutically-acceptable salt, or biohydrolyzable amide, ester, or imide thereof are useful as inhibitors of metallop
2-SACCHARINYLMETHYL ARYL CARBOXYLATES USEFUL AS PROTEOLYTIC ENZYME INHIBITORS AND COMPOSITIONS AND METHOD OF USE THEREOF
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, (2008/06/13)
A compound having the formula: STR1 wherein Ar, R 4 and R 5 are defined herein have pharmaceutical utility as proteolytic enzyme inhibitors.
2-SACCHARINYLMETHYL PHOSPHATES, PHOSPHONATES AND PHOSPHINATES USEFUL AS PROTEOLYTIC ENZYME INHIBITORS AND COMPOSITIONS AND METHOD OF USE THEREOF
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, (2008/06/13)
4-R 1-R 2-R 3-2-Saccharinylmethyl and 4,7-C-4,5, 6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates of formulas I and IIA respectively herein, useful in the treatment of degenerative diseases, and compositions containing them, methods for using them to treat degenerative diseases, and processes for their preparation by reaction of the corresponding 2-halomethylsaccharins with a phosphate, phosphonate or phosphinic acid of formula III herein in the presence of an acid-acceptor.