28281-58-5Relevant academic research and scientific papers
Combining Photodeprotection and Ligation into a Dual-Color Gated Reaction System
Alves, Jessica,Krappitz, Tim,Feist, Florian,Blinco, James P.,Barner-Kowollik, Christopher
, p. 16985 - 16989 (2020)
We report a photochemical reaction system which requires activation by two colors of light. Specifically, a dual wavelength gated system is established by fusing the visible light mediated deprotection of a dithioacetal with the UV light activated Diels–A
Directed regioselective lithiation of (η6-arene) chromium tricarbonyl complexes. Regioselective synthesis of anthraquinones and calamenenes
Uemura, Motokazu,Take, Kazuhiko,Isobe, Kazuo,Minami, Tatsuya,Hayashi, Yuji
, p. 5771 - 5778 (1985)
(3-Methoxybenzylalcohol)chromium tricarbonyl (10) and (7-methoxy-1-tetralol)chromium tricarbonyl (12) are selectively lithiated at the 4- and 6-positions, respectively, by treatment with n-BuLi-TMEDA. Since the directed lithiation of the corresponding chromium free arenes normally proceeds at the 2-and 8-positions, complementarily substituted arenes can be prepared by using the chromium tricarbonyl complexes. The difierent position of lithiation is explained by the relative configuration of the chromium tricarbonyl group in the (arene)Cr(CO)3 and electrostatic factors. Some anthraquinones, 31,36,42, and 7-hydroxycalamenenes, 43, have been synthesized through the stereo- and regioselective introduction of substituents by means of(η6-arene)chromium tricarbonyl complexes.
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
supporting information, p. 224 - 239 (2017/12/08)
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
Regiocontrolled rearrangement of isobenzofurans
Egan, Ben A.,Paradowski, Michael,Thomas, Lynne H.,Marquez, Rodolfo
supporting information; experimental part, p. 2086 - 2089 (2011/06/25)
Regioselective alkylation and oxidative rearrangement of isobenzofurans has been achieved to generate substituted 4,8- ihydroxyisochromanones in good yields and with complete regiocontrol.
Stereoselective total synthesis of (+)-varitriol
Srinivas,Sridhar,Rao, K. Rama
scheme or table, p. 8527 - 8535 (2010/11/18)
Stereoselective total synthesis of (+)-varitriol, an antitumor natural product, was accomplished by two versatile strategies starting from the commercially available d-(-)-ribose and ethyl (S)-lactate. The key steps involved in the synthesis of the target molecule are epoxidation, cyclization, dihydroxylation and Diels-Alder reaction.
INDOLYLMALEIMIDE DERIVATIVES
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Page/Page column 50-51, (2008/06/13)
A compound of formula (I) wherein R, R1, and R2, ring A and ring B are as defined in the specification, processes for their production, their uses, in particular in transplantation, and pharmaceutical compositions containing them.
Studies toward the total synthesis of mumbaistatin, a highly potent glucose-6-phosphate translocase inhibitor. Synthesis of a mumbaistatin analogue
Kaiser, Florian,Schwink, Lothar,Velder, Janna,Schmalz, Hans-Guenther
, p. 9248 - 9256 (2007/10/03)
A strategy for the total synthesis of the highly potent glucose-6-phosphate translocase inhibitor mumbaistatin (1) and structural analogues was elaborated. Such compounds represent a lead structure in the development of potential new drugs for the treatment of diabetes. To evaluate the general strategy, the close mumbaistatin analogue 10 was synthesized in a convergent manner. The anthraquinone building block 20 was efficiently prepared via aryne/phthalide annulation. After conversion of 20 into the corresponding 9,10-dimethoxyanthracene-1-carbaldehyde derivative (13), coupling with a lithiated arene (12) and subsequent multiple oxidation under Jones conditions yielded the mumbaistatin analogue 10. The preparation of the functionalized arene intermediates was achieved exploiting highly regioselective bromination and ortho-lithiation reactions.
Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates
Dang, Qun,Brown, Brian S.,Van Poelje, Paul D.,Colby, Timothy J.,Erion, Mark D.
, p. 1505 - 1510 (2007/10/03)
A new prodrug approach for intracellular delivery of phosphonates was developed via the synthesis of 3-phthalidyl esters of 1- naphthalenemethylphosphonate. This approach is advantageous over the traditional acyloxymethyl phosphonate prodrugs, because the
Trisubstituted benzene leukotriene B4 receptor antagonists: Synthesis and structure-activity relationships
Konno, Mitoshi,Nakae, Takahiko,Sakuyama, Shigeru,Odagaki, Yoshihiko,Nakai, Hisao,Hamanaka, Nobuyuki
, p. 1649 - 1674 (2007/10/03)
A series of trisubstituted benzenes which demonstrate leukotriene B4 (LTB4, 1) receptor affinity was prepared. Previous trisubstituted benzenes from our laboratory showed high affinity to the LTB4 receptor but demonstrated
Studies on Carboxylation of Alkoxy-Substituted Benzyl Alcohols via Direct Lithiation and Bromine-Lithium Exchange: Synthesis of Phthalides and Phthalideisoquinoline Alkaloids
Orito, Kazuhiko,Miyazawa, Mamoru,Suginome, Hiroshi
, p. 2489 - 2496 (2007/10/02)
Conversion of alkoxy-substituted benzyl alcohols to the corresponding phthalides by carboxylation via ortho lithiation and bromine-lithium exchange was studied.The method was applied to the key step in the synthesis of phthalideisoquinoline alkaloids.
