129099-61-2Relevant academic research and scientific papers
TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane
Hartmann, Peter,Lazzarotto, Mattia,Steiner, Lorenz,Cigan, Emmanuel,Poschenrieder, Silvan,Sagmeister, Peter,Fuchs, Michael
, p. 5831 - 5837 (2019/04/25)
The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40-47% overall yield along four-step synthetic routes.
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.
Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones
Landais,Robin,Lebrun
, p. 3787 - 3804 (2007/10/02)
Ruthenium (IV) dioxide dihydrate in fluoro acid medium was found to be a very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.
AN EFFICIENT SYNTHESIS OF NATURAL (+)-NEOISOSTEGANE USING ASYMMETRIC HYDROGENATION CATALYZED BY A CHIRAL BISPHOSPHINE-RHODIUM(I) COMPLEX
Morimoto, Toshiaki,Chiba, Mitsuo,Achiwa, Kazuo
, p. 363 - 366 (2007/10/02)
(+)-Neoisostegane, a natural lignan lactone was synthesized by utilizing a catalytic asymmetric hydrogenation of α-veratrylidenesuccinic acid half-ester with a (S,S)-MOD-DIOP-rhodium(I) as a key step, and the absolute configuration was determined to be (M
LE TETRAKIS(TRIFLUOROACETATE) DE RUTHENIUM(IV), NOUVEAU CATALYSEUR A TEMPERATURE AMBIANTE DU COUPLAGE BIARYLIQUE OXIDANT NON PHENOLIQUE-PREMIERE SYNTHESE TOTALE BIOMIMETIQUE DU NEOISOSTEGANE-
Landais, Y.,Robin, J.-P.
, p. 1785 - 1788 (2007/10/02)
In situ generated Ruthenium(IV) tetrakis(trifluoroacetate) -a new organometallic reagent- was used in intramolecular non-phenolic oxydative biaryl coupling of dibenzylbutanolides, and an application to the first total synthesis of neoisostegane was perfor
