20007-99-2Relevant articles and documents
Annulative Ring Expansions. Direct Conversion of ω-Alkynyl Acetals to Polycyclic Unsaturated Ketones
Sisko, Joseph,Balog, Aaron,Curran, Dennis P.
, p. 4341 - 4342 (1992)
Geminal acylation of ω-acetylenic acetals and bis(silyloxy)cycloalkenes under Lewis acid conditions preceded cationic cyclization of the alkyne onto the ketone to produce polycyclic unsaturated ketones.
Identification of Inhibitors of Cholesterol Transport Proteins Through the Synthesis of a Diverse, Sterol-Inspired Compound Collection
Laraia, Luca,Olsen, Asger Hegelund,Whitmarsh-Everiss, Thomas
supporting information, p. 26755 - 26761 (2021/11/17)
Cholesterol transport proteins regulate a vast array of cellular processes including lipid metabolism, vesicular and non-vesicular trafficking, organelle contact sites, and autophagy. Despite their undoubted importance, the identification of selective modulators of this class of proteins has been challenging due to the structural similarities in the cholesterol-binding site. Herein we report a general strategy for the identification of selective inhibitors of cholesterol transport proteins via the synthesis of a diverse sterol-inspired compound collection. Fusion of a primary sterol fragment to an array of secondary privileged scaffolds led to the identification of potent and selective inhibitors of the cholesterol transport protein Aster-C, which displayed a surprising preference for the unnatural-sterol AB-ring stereochemistry and new inhibitors of Aster-A. We propose that this strategy can and should be applied to any therapeutically relevant sterol-binding protein.
A synthetic approach to (±)-aristomakine
Perni, Robert B.,Gribble, Gordon W.
, p. 75 - 84 (2018/07/03)
We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (±)-aristomakine (1) from 2, 15, or derivatives have not been successful.
One-pot synthesis of Wieland-Miescher ketone by enzymes
Lai, Yi-Feng,Zhang, Peng-Fei
, p. 4077 - 4082 (2015/06/30)
We first report that lipase from porcine pancreas catalyzed Robinson annulation in the organic media to synthesize the Wieland-Miescher ketone. The promiscuous catalytic activity of lipase in the Robinson reaction is due to an important role played by lipase activity in both the Michael addition and Aldol reaction.
Prolinamide/PPTS-catalyzed Hajos-Parrish annulation: Efficient approach to the tricyclic core of cylindricine-type alkaloids
Zhang, Xiao-Ming,Wang, Min,Tu, Yong-Qiang,Fan, Chun-An,Jiang, Yi-Jun,Zhang, Shu-Yu,Zhang, Fu-Min
scheme or table, p. 2831 - 2835 (2009/05/07)
A series of Wieland-Miescher ketone analogues bearing highly functionalized substituents are efficiently constructed in high enantioselectivities and good yields using catalytic amounts of prolinamide and PPTS. We have successfully utilized this reaction as a key step to synthesize the tricyclic core of cylindricine type alkaloids. Georg Thieme Verlag Stuttgart.
Evaluating β-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction
Davies, Stephen G.,Russell, Angela J.,Sheppard, Ruth L.,Smith, Andrew D.,Thomson, James E.
, p. 3190 - 3200 (2008/03/14)
A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3- amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to l-proline. The Royal Society of Chemistry.
Bimorpholine-mediated enantioselective intramolecular and intermolecular aldol condensation
Kanger, Tonis,Kriis, Kadri,Laars, Marju,Kailas, Tiiu,Mueuerisepp, Aleksander-Mati,Pehk, Tonis,Lopp, Margus
, p. 5168 - 5173 (2008/02/08)
(Chemical Equation Presented) Monosalts of N-substituted bimorpholine derivatives are efficient organocatalysts in intramolecular and intermolecular aldol reactions. The properties of the catalysts can be tuned either by the selection of an appropriate acid for the salt formation or by the change of a substituent at the nitrogen atom. In aldol condensation, i-Pr-substituted bimorpholine is the most stereoselective catalyst affording products in high yield with enantioselectivities up to 95% ee.
Synthesis and use of 3,3′-bimorpholine derivatives in asymmetric Michael addition and intramolecular aldol reaction
Sulzer-Mosse, Sarah,Laars, Marju,Kriis, Kadri,Kanger, Tonis,Alexakis, Alexandre
, p. 1729 - 1732 (2008/02/08)
The synthesis of 3,3′-bimorpholine and its N-alkyl derivatives is described. These new diamine derivatives were revealed to be efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroalkenes with excellent enantioselectivity (up to 90% ee). The potential of these organocatalysts was also demonstrated for the highly enantioselective intramolecular aldol reaction affording the Wieland-Miescher ketone with tremendous enantioselectivity (up to 95% ee). Georg Thieme Verlag Stuttgart.
Enantioselective synthesis of Wieland-Miescher ketone through bimorpholine-catalyzed organocatalytic aldol condensation
Kriis, Kadri,Kanger, T?nis,Laars, Marju,Kailas, Tiiu,Müürisepp, Aleksander-Mati,Pehk, T?nis,Lopp, Margus
, p. 1699 - 1702 (2008/02/03)
Novel bimorpholine-derived organocatalysts have been used for highly enantioselective intramolecular aldol reaction affording Wieland-Miescher ketone in high yield and enantioselectivity (up to 92% and 95%, respectively). Georg Thieme Verlag Stuttgart.
Promotion of one-pot Robinson annelation achieved by gradual pressure and temperature manipulation under supercritical conditions
Kawanami, Hajime,Ikushima, Yutaka
, p. 5147 - 5150 (2007/10/03)
The one-pot Robinson annelation from 2-methyl-cyclohexane-1,3-dione with 3-buten-2-one can be achieved in high yield (95%) and high selectivity (95%) by pressure and temperature manipulation using supercritical carbon dioxide in the presence of MgO catalyst, whose method could be applied for various ketones to synthesize fused polycyclic compounds.
