109987-02-2Relevant academic research and scientific papers
Total synthesis of(±)-neovibsanin b
Imagawa, Hiroshi,Saijo, Hayato,Kurisaki, Takahiro,Yamamoto, Hirofumi,Kubo, Miwa,Fukuyama, Yoshiyasu,Nishizawa, Mugio
, p. 1253 - 1255 (2009)
(±)-Neovibsanin B was synthesized based on a DMI-accelerated intramolecular Diels-Alder reaction followed by oxy-Michael addition- lactonization. The synthetic (±)-neovibsanin B induced similar morphological changes in NGF-mediated PC12 cells compared wit
Use of 4-cyanocoumarins as dienophiles in a facile synthesis of highly substituted dibenzopyranones
Jung, Michael E.,Allen, Damian A.
, p. 757 - 760 (2009)
(Chemical Equation Presented) A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.
Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers
Davies, Thomas Q.,Murphy, John J.,Dousset, Maxime,Fürstner, Alois
supporting information, p. 13489 - 13494 (2021/09/11)
Nickel catalysis allied with cyclodiphosphazane or VAPOL-derived phosphoramidite ligands provides selective access to monoprotected vicinal diols by reductive coupling of dienol ethers and aldehydes. The observed regioselectivity is unprecedented, in that the diene reacts at the least nucleophilic and most hindered C atom that is attached to the oxygen substituent rather than at the terminal position. Notably, both syn and anti diastereomers of the products can be accessed depending on the configuration of the diene partner with usually excellent diastereo- and enantioselectivity.
Stereocontrolled Synthesis of a Potential Transition-State Inhibitor of the Salicylate Synthase MbtI from Mycobacterium tuberculosis
Liu, Zheng,Liu, Feng,Aldrich, Courtney C.
, p. 6545 - 6552 (2015/10/06)
Mycobactins are small-molecule iron chelators (siderophores) produced by Mycobacterium tuberculosis (Mtb) for iron mobilization. The bifunctional salicylate synthase MbtI catalyzes the first step of mycobactin biosynthesis through the conversion of the primary metabolite chorismate into salicylic acid via isochorismate. We report the design, synthesis, and biochemical evaluation of an inhibitor based on the putative transition state (TS) for the isochorismatase partial reaction of MbtI. The inhibitor mimics the hypothesized charge buildup at C-4 of chorismate in the TS as well as C-O bond formation at C-6. Another important design element of the inhibitor is replacement of the labile pyruvate side chain in chorismate with a stable C-linked propionate isostere. We developed a stereocontrolled synthesis of the highly functionalized cyclohexene inhibitor that features an asymmetric aldol reaction using a titanium enolate, diastereoselective Grignard addition to a tert-butanesulfinyl aldimine, and ring closing olefin metathesis as key steps.
The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity
B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg
supporting information, p. 2524 - 2532 (2014/11/08)
A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.
The 'Mikami'-Catalyst in Enantioselective Diels-Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity
B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg
supporting information, p. 2524 - 2532 (2015/12/26)
A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed- Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.
A Diels-Alder approach to biaryls (DAB): synthesis of the western portion of TMC-95
Ashburn, Bradley O.,Rathbone, Lauren K.,Camp, Elizabeth H.,Carter, Rich G.
, p. 856 - 865 (2008/09/16)
The rapid synthesis of the western biaryl portion of TMC-95 is disclosed via the use of a Diels-Alder reaction with o-nitrostyrene derivative and 1-silyloxy diene with excellent regiochemical control. Subsequent sequential substitutions of a p-iodo-phenol
From 1-(Silyloxy)butadiene to 4-Amino-4-deoxy-DL-erythrose and to 1-Amino-1-deoxy-DL-erythriol Derivatives via hetero-Diels-Alder Reactions with Acylnitroso Dienophiles
Defoin, Albert,Pires, Joaquim,Streith, Jacques
, p. 1653 - 1670 (2007/10/02)
Acylnitroso dienophiles 4 reacted instantly with 1-(silyloxy)butadiene 5α and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table 1). cis-Hydroxylation of these primary cycloadducts with OsO4 (catalyst) occurred stereospecifically and in high yield (-> 8 and 9, resp.: Scheme 2).It was followed by reductive ring cleavage to give either 1-amino-1-deoxy-DL-erythriol or 4-amino-4-deoxy-DL-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4).
