115061-18-2Relevant academic research and scientific papers
Efficient synthesis of lactonic and thionolactoniclignans and evaluation of their anti-oxidant, anti-inflammatory and cytotoxic activities
Golakoti, Trimurtulu,Kancharla, Hari Krishna,Meka, Bharani,Murthy
, p. 2906 - 2915 (2016/11/09)
A short and versatile synthesis of α,β-dibenzyl-γ-butyrolactones has been developed starting from inexpensive materials by applying Stobbe condensation and following the novel reductive cyclisation with sodiumborohydride. Natural products Suchilactone (5a
Synthesis and cytotoxicity of racemic isodeoxypodophyllotoxin analogues with isoprene-derived side chains
Zhao, Yu,Feng, Ju Hong,Ding, Hong Xia,Xiong, Yi,Cheng, Christopher H. K.,Hao, Xiao Jiang,Zhang, Yong Min,Pan, Yuan Jiang,Gueritte, Francoise,Wu, Xiu Mei,Bai, Hua,Stoeckigt, Joachim
, p. 1145 - 1152 (2008/09/21)
A series of isodeoxypodophyllotoxin (5) analogues, 26-38, with various isoprene-derived side chains at the E-ring were designed and synthesized. For comparison, compound 39, with a benzyloxy group on the E-ring, and six D-ring opened analogues, 40-45, were also prepared. All the synthetic compounds were evaluated for their cytotoxic activities in vitro against seven cultured human tumor cell lines. Compounds 27, 43, and 44 were more cytotoxic than etoposide on BEL-7404, A549, and HL-60 cell lines, respectively. However, none of the synthetic isodeoxypodophyllotoxins were more cytotoxic than podophyllotoxin (1).
An Easy Procedure for the Preparation of 3-Methylidenetetrahydrofurans from Dimethyl Succinates
Corral, Jose M. Miguel,Gordaliza, Marina,Castro, M. Angeles,Salinero, Miguel A.,Dorado, Jose M.,Feliciano, Arturo San
, p. 154 - 164 (2007/10/03)
A new synthetic proceduree to obtain 3-methylidenetetrahydrofurans is described, in which the methylidene group is generated during the formation of the tetrahydrofuran ring. These are prepared by reduction of differently substituted dimethyl succinates obtained by Stobbe condensation.
Efficient Asymmetric Syntheses of Naturally Occurring Lignan Lactones Using Catalytic Asymmetric Hydrogenation as a Key Reaction
Morimoto, Toshiaki,Chiba, Mitsuo,Achiwa, Kazuo
, p. 1793 - 1806 (2007/10/02)
Optically pure (R)-arylmethylsuccinic acid mono-methyl esters were obtained efficiently by using the catalytic asymmetric hydrogenation of arylidenesuccinic acid monoesters with a rhodium(I) complex of a chiral bisphosphine, (4S,5S)-MOD-DIOP.Asymmetric total syntheses of some naturally occurring lignans, (+)-collinusin, (-)-deoxypodophyllotoxin, and (+)-neoisostegane, were achieved via several steps from (R)-γ-butyrolactones as key intermediates obtained by reduction of (R)-arylmethylsuccinic acid mono methyl-esters.
Oxidative Coupling of Lignans. III. Non-Phenolic Oxidative Coupling of Deoxypodorhizon and Related Compounds
Cambie, Richard C.,Craw, Peter A.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 897 - 918 (2007/10/02)
Oxidative coupling of deoxypodorhizon (4) with thallium(III) oxide and trifluoroacetic acid may be controlled to give either deoxyisopodophyllotoxin (14) or isostegane (16).These results and those with related non-phenolic substances indicate that the aromatic substituents of the parent diarylbutane play an important role in determining the outcome of oxidative coupling.
The Wittig Reaction of 2-t-Butoxycarbonyl-1-methoxycarbonylethylidenetriphenylphosphorane: A Surrogate for Stobbe Reaction
Rizzacasa, Mark A.,Sargent, Melvyn V.
, p. 1737 - 1743 (2007/10/02)
The reaction of 2-t-butoxycarbonyl-1-methoxycarbonylethylidenetriphenylphosphorane (3) with a range of aromatic aldehydes has been explored.The resultant itaconic esters, obtained in high yield, are readily converted into methyl 4-acetoxynaphthalene-2-carboxylates.
Synthesis of 3,4-Bis-dihydro-2(3H)-furanones and 2,3-Bis(m- or p-substituted-benzyl)-butane-1,4-diols.
Neelima,Bhaduri, A. P.
, p. 209 - 215 (2007/10/02)
Stobbe condensation of appropriately substituted aromatic aldehydes with diethyl or dimethyl succinate in the presence of sodium methoxide yields the required starting materials for the synthesis of the title compounds.The diacids (1-4) and half acid-half
Synthesis of Aryltetralin and Dibenzylbutyrolactone Lignans: (+/-)-Lintetralin, (+/-)-Phyltetralin, and (+/-)-Kusunokinin
Ganeshpure, Pralhad A.,Stevenson, Robert
, p. 1681 - 1684 (2007/10/02)
Application of a general synthetic pathway for aryltetralin and dibenzylbutyrolactone lignans, starting from the lithium enolate of 3-(3,4-dimethoxybenzyl)butyrolactone (1) led to syntheses of (+/-)-lintetralin (4), (+/-)-phyltetralin (5), (+/-)-isogalcat
