93578-48-4Relevant academic research and scientific papers
Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol
Roy, Subhas Chandra,Rana, Kalyan Kumar,Guin, Chandrani
, p. 3242 - 3248 (2007/10/03)
Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo [3.3.0] octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether lb, acuminatin methyl ether le, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin li, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.
Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate)
Ward, Robert S,Hughes, David D
, p. 2057 - 2064 (2007/10/03)
A series of trans-3,4-dibenzyltetrahydrofurans has been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate), affording dibenzocyclooctadiene lignans belonging to the isostegane series, in high yields. Since no evidence was found for the formation of the corresponding stegane isomers it is assumed that the reactions proceed with complete diastereoselectivity.
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
