671232-60-3Relevant academic research and scientific papers
A formal anti-Markovnikov hydroalkoxylation of allylic alcohols with a ruthenium catalyst
Nakamura, Yushi,Ohta, Tetsuo,Oe, Yohei
supporting information, p. 288 - 291 (2018/02/14)
Hydroalkoxylation of C-C double bonds was achieved through the use of a ruthenium catalyst. The reaction of allylic alcohols with nucleophilic alcohols was carried out in the presence of a ruthenium catalyst prepared by RuClH(CO)(PPh3)3 and 2,6-bis(n-butyliminomethyl)-4-(piperidin-1-yl)pyridine under mild reaction conditions to afford the corresponding γ-alkoxypropanols in good yield.
Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
Dieckmann, Michael,Menche, Dirk
supporting information, p. 228 - 231 (2013/03/28)
A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydrox
Chemo-enzymatic asymmetric total synthesis of stagonolide-C
Jana, Nandan,Mahapatra, Tridib,Nanda, Samik
experimental part, p. 2622 - 2628 (2010/03/25)
The naturally occurring phytotoxic noneolide stagonolide-C has been synthesized by a chemo-enzymatic approach. Two key intermediates have been synthesized by applying a metal-enzyme combined DKR (dynamic kinetic resolution) strategy, followed by RCM (ring
Evaluating the potential of Vacuolar ATPase inhibitors as anticancer agents and multigram synthesis of the potent salicylihalamide analog saliphenylhalamide
Lebreton, Sylvain,Jaunbergs, Janis,Roth, Michael G.,Ferguson, Deborah A.,De Brabander, Jef K.
scheme or table, p. 5879 - 5883 (2009/06/25)
The natural product salicylihalamide is a potent inhibitor of the Vacuolar ATPase (V-ATPase), a potential target for antitumor chemotherapy. We generated salicylihalamide-resistant tumor cell lines typified by an overexpansion of lysosomal organelles. We also found that many tumor cell lines upregulate tissue-specific plasmalemmal V-ATPases, and hypothesize that tumors that derive their energy from glycolysis rely on these isoforms to maintain a neutral cytosolic pH. To further validate the potential of V-ATPase inhibitors as leads for cancer chemotherapy, we developed a multigram synthesis of the potent salicylihalamide analog saliphenylhalamide.
A total synthesis of hydroxylysine in protected form and investigations of the reductive opening of p-methoxybenzylidene acetals
Gustafsson, Tomas,Schou, Magnus,Almqvist, Fredrik,Kihlberg, Jan
, p. 8694 - 8701 (2007/10/03)
A synthesis of (2S,5R)-5-hydoxylysine, based on (R)-malic acid and Williams glycine template as chiral precursors, has been developed. This afforded hydroxylysine, suitably protected for direct use in peptide synthesis, in 32% yield over the 13-step sequence. Regioselective reductive opening of a p-methoxybenzylidene acetal and alkylation of the Williams glycine template were key steps in the synthetic sequence. Surprisingly, the regioselectivity in opening of the p-methoxybenzylidene acetal was reversed as compared to what was expected. It was found that this was due to chelation of the trialkylsilyl choride, used as an electrophile in the reductive opening, to an adjacent azide functionality. It was also discovered that an equivalent amount of trialkylsilyl hydride was formed in the reaction, a finding that led to additional mechanistic insight into reductive openings of p-methoxybenzylidene acetals with sodium cyanoborohydride as reducing agent.
Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: Application in the formal synthesis of macrosphelide A
Chakraborty, Tushar K.,Purkait, Subhas,Das, Sanjib
, p. 9127 - 9135 (2007/10/03)
An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transfor
