77545-60-9Relevant academic research and scientific papers
Concise Total Syntheses of (±)-Joubertiamine, (±)- O -Methyljoubertiamine, (±)-3′-Methoxy-4′- O -methyljoubertiamine, (±)-Mesembrane, and (±)-Crinane
Das, Mrinal Kanti,De, Subhadip,Bisai, Alakesh
, p. 2093 - 2104 (2016/07/06)
A method to access cis-3a-aryloctahydroindole alkaloids has been developed through a key strategy involving Eschenmoser-Claisen rearrangement of allylalcohol. This approach gives us an opportunity to access the all-carbon quaternary center required for ci
Concise total syntheses of (±)-mesembrane and (±)-crinane
Das, Mrinal Kanti,De, Subhadip,Shubhashish,Bisai, Alakesh
supporting information, p. 3585 - 3588 (2015/03/30)
A straightforward and unified strategy to access Amaryllidaceae alkaloids comprising a cis-3a-aryloctahydroindole scaffold has been developed. The strategy features Eschenmoser-Claisen rearrangement of allylalcohol as a key step for the installation of al
Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones
Cheng, Li-Jie,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
supporting information; experimental part, p. 1105 - 1113 (2012/05/21)
A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (-)-CP-55940 has been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2-SDPs/ diamine [SDPs=7,7'-bis(diarylphophino)-1,1'-spirobiindane] catalysts the asymmetric hydrogenation of racemic α-arylcyclohexanones via DKR provided the corresponding cis-β-arylcyclohexanols in high yields with up to 99.3% ee and >99:1 cis-selectivities. Both ethylene ketal group at the cyclohexane ring and ortho-methoxy group at the phenyl ring of the substrates 6 have little effect on the selectivity and reactivity of the hydrogenations. Based on this highly efficient asymmetric ketone hydrogenation, (-)-CP-55940 was synthesized in 13 steps (the longest linear steps) in 14.6% overall yield starting from commercially available 3-methoxybenzaldehyde and 1,4-cyclohexenedione monoethylene acetal. Copyright
Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one
Fall, Yacoub,Doucet, Henri,Santelli, Maurice
experimental part, p. 489 - 495 (2009/04/07)
The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentan
Methods and Compositions to Inhibit Edema Factor and Adenylyl Cyclase
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, (2009/04/24)
Small molecules and their derivatives are described for the treatment and/or prevention of intestinal fluid loss. Also disclosed are methods of using said molecules and their derivatives to treat and/or prevent conditions associated with increased levels
Synthesis and screening of small molecule inhibitors of anthrax edema factor
Jimenez, Maria Estrella,Bush, Kathryn,Pawlik, Jennifer,Sower, Laurie,Peterson, Johnny W.,Gilbertson, Scott R.
supporting information; experimental part, p. 4215 - 4218 (2009/04/07)
The synthesis and development of a novel class of molecules that inhibit anthrax edema factor, an adenylyl cyclase, is reported. These molecules are derived from the initial discovery that histidine and imidazole adducts of the prostaglandin PGE2 reduce the net secretory response of cholera toxin-challenged mice and act directly on the action of anthrax edema factor, a calmodulin-dependent adenylyl cyclase. The simple enones examined in this letter were prepared by palladium-catalyzed Suzuki reaction.
An efficient synthesis of (±)-crinane using an intramolecular azide-olefin cycloaddition
Schkeryantz, Jeffrey M.,Pearson, William H.
, p. 3107 - 3116 (2007/10/03)
Refluxing 3-(2-azidoethyl)-3-[3,4-(methylenedioxy)phenyl]cyclohex-1-ene (2) in toluene for 24 hours afforded 3a-[3,4-methylenedioxy)phenyl]-3,3a,4,5,6,7-hexahydro-2H-indole (12) in quantitative yield. This reaction proceeds by intramolecular 1,3-dipolar cycloaddition of the azide onto the alkene followed by loss of nitrogen from the triazoline intermediate to give an imine. Reduction of the imine 12 with sodium cyanoborohydride in acetic acid/THF gave (3aR*, 7aR*)-3a-[3,4-methylenedioxy)phenyl]-2,3,3a,4,5,6,7,7a-octahydroindol e (13). Warming 13 with Eschenmoser's salt provided (±)-crinane (1). The synthesis of (±)-crinane (1) from cyclohexenone was accomplished in 8 steps in 23% overall yield.
