638-37-9Relevant articles and documents
Epoxide-opening cascades triggered by a Nicholas reaction: Total synthesis of teurilene
Rodríguez-L?pez, Julio,Pinacho Cris?stomo, Fernando,Ortega, Nuria,L?pez-Rodríguez, Matías,Martín, Víctor S.,Martín, Tomás
, p. 3659 - 3662 (2013)
Natural inspiration: Based on the biosynthesis of squalene-derived polyethers, a total synthesis of teurilene is described. The carbocation formation in the Nicholas reaction serves to control the initiation of a polyepoxide ring-opening cascade. The three furan rings present in teurilene were obtained in excellent yield in one step. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl. Copyright
2:2 condensation products from the reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes with succinaldehyde and glutaraldehyde
Okawara, Tadashi,Okamoto, Yoshinari,Ehara, Shuji,Yamasaki, Tetsuo,Furukawa, Mitsuru
, p. 2487 - 2493 (1996)
The reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes (1) with succinaldehyde (2) and glutaraldehyde (9) in water gave the 2:2 condensation products (4 and 10).
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Sutter
, p. 59 (1932)
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Diastereoselective Synthesis of Cyclic Five-Membered trans,trans-Configured Nitrodiols by Double Henry Reaction of 1,4-Dialdehydes
Fr?hlich, Janine,Lehmkuhl, Kirstin,Fr?hlich, Roland,Wünsch, Bernhard
, p. 589 - 594 (2015)
Conformationally constrained perhydroquinoxalines 4 show high κ receptor affinity, selectivity over related receptors and full agonistic activity. Since the κ affinity can be correlated with the dihedral angle of the ethylenediamine pharmacophore (4a: 55°/71°), the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. The first step of the synthesis represents a double Henry reaction of 1,4-dialdehydes 8 and 10 with nitromethane, leading predominantly to the trans,trans-configured nitrodiols 9 and 11. X-ray crystal structure analyses of 9 and 11 led to dihedral angles O2N-C-C-OH of 73.4 and 88.3°, respectively, which reflect the calculated dihedral angles of the hypothesized final products 5a and 6a. Since κ receptor affinity can be correlated with the dihedral angle of ethylenediamine pharmacophores, the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. X-ray crystal structure analyses of the synthesized compounds 9 and 11 led to dihedral angles of 73.4 and 88.3°, respectively, reflecting the calculated dihedral angles of the hypothesized final products 5a and 6a.
Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12-Prostaglandin J3
Pel?s, Andrejs,Gandhamsetty, Narasimhulu,Smith, James R.,Mailhol, Damien,Silvi, Mattia,Watson, Andrew J. A.,Perez-Powell, Isabel,Prévost, Sébastien,Schützenmeister, Nina,Moore, Peter R.,Aggarwal, Varinder K.
, p. 9542 - 9545 (2018)
Re-investigation of the l-proline catalyzed double aldol cascade dimerization of succinaldehyde for the synthesis of a key bicyclic enal intermediate, pertinent in the field of stereoselective prostaglandin synthesis, is reported. The yield of this process has been more than doubled, from 14 % to a 29 % isolated yield on a multi-gram scale (32 % NMR yield), through conducting a detailed study of the reaction solvent, temperature, and concentration, as well as a catalyst screen. The synthetic utility of this enal intermediate has been further demonstrated through the total synthesis of Δ12-prostaglandin J3, a compound with known anti-leukemic properties.
Direct catalytic synthesis of β-(C3)-substituted pyrroles: A complementary addition to the Paal-Knorr reaction
Pawar, Amol Prakash,Yadav, Jyothi,Mir, Nisar Ahmad,Iype, Eldhose,Rangan, Krishnan,Anthal, Sumati,Kant, Rajni,Kumar, Indresh
supporting information, p. 251 - 254 (2021/01/13)
The synthesis of β-(C3)-functionalized pyrroles is a challenging task and requires a multistep protocol. An operationally simple direct catalytic synthesis of β-substituted pyrroles has been developed. This one-pot multicomponent method combined aqueous succinaldehyde as 1,4-dicarbonyl, primary amines, and isatins to access hydroxyl-oxindole β-tethered pyrroles. Direct synthesis of the β-substituted free NH-pyrrole is the central intensity of this work. DFT-calculations and preliminary mechanism investigation support the possible reaction pathway. This journal is
Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence
Chen, Huiyu,Lu, Xiuxiang,Tan, Haibo,Wang, Sasa,Zhang, Wenge,Zheng, Anquan,Zhou, Tingting
, (2021/09/03)
A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.
