102191-92-4Relevant articles and documents
Synthetic Studies toward the C14-C29 Fragment of Mirabalin
Cornil, Johan,Echeverria, Pierre-Georges,Reymond, Sébastien,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Guérinot, Amandine,Cossy, Janine
, p. 4534 - 4537 (2016)
A convergent synthesis of one isomer of the C14-C29 fragment of mirabalin is disclosed. The key steps include a Marshall allenylation, a Mukaiyama aldol reaction and a Crimmins aldolization, which allow the control of 10 out of 25 stereogenic centers pres
Novel synthesis of the ocular age pigment A2-E: new method for substituted pyridine synthesis via azaelectrocyclization.
Tanaka,Katsumura
, p. 373 - 375 (2000)
[reaction: see text] The formal synthesis of the ocular age pigment A2-E was achieved by the efficient one-pot preparation of the substituted pyridine, which involves the aza-6pi-electrocyclization of the Schiff base derived from (E)-3-carbonyl-2,4,6-trienal followed by oxidation.
First highly efficient asymmetric synthesis of the Hyrtios erectus diketotriterpenoid
Enders, Dieter,Schuesseler, Thomas
, p. 2280 - 2288 (2002)
The first highly efficient asymmetric synthesis of the diketotriterpenoid 1, isolated from the Indonesian marine sponge Hyrtios erectus, in good overall yield and employing simple starting materials such as butanone, is described. Both stereogenic centres at the C-6 and C-19 positions of the C2-symmetrical molecule were generated via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric inductions (de, ee ≥ 96%). The absolute configuration of the natural material was determined as R,R.
Synthesis and in vitro activity evaluation of 2',3'-c-dimethyl carbocyclic nucleoside analogues as potential anti-HCV agents
Ko, Ok Hyun,Hong, Joon Hee
, p. 761 - 771 (2009)
The first synthetic route of novel 2'(β),3'(β)-C-dimethyl carbodine analogues is described. The key intermediate cyclopentenyl alcohol 11(β) prepared from Weinreb amide 4 via ring-closing metathesis (RCM) and vicinal dihydroxylation. Coupling of 12 with n
Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones
Lagoutte, Roman,Pastor, Miryam,Berthet, Mathéo,Winssinger, Nicolas
, p. 6012 - 6021 (2018)
The sesquiterpene lactones cover a diverse and pharmacologically important diversity space. In particular, the electrophilic α-exo-methylene-γ-butyrolactone moiety that is preponderant in this natural product family has been shown to readily engage in cov
Synthetic study toward total synthesis of (±)-germine: Synthesis of (±)-4-methylenegermine
Stork, Gilbert,Yamashita, Ayako,Hanson, Robert M.,Phan, Ly,Phillips, Eifion,Dubé, Daniel,Bos, Pieter H.,Clark, Andrew J.,Gough, Maxwell,Greenlee, Mark L.,Jiang, Yimin,Jones, Keith,Kitamura, Masato,Leonard, John,Liu, Tongzhu,Parsons, Philip J.,Venkatesan, Aranapakam M.
, p. 5150 - 5153 (2017)
The total synthesis of 4-methylenegermine is described.
Formal synthesis of belactosin A and hormaomycin via a diastereoselective intramolecular cyclopropanation of an α-nitro diazoester
Vanler, Sebastien F.,Larouche, Guillaume,Wurz, Ryan P.,Charette, Andre B.
, p. 672 - 675 (2010)
Chemical Equation presented An efficient and convenient methodology for the synthesis of the 3-(trans-2-aminocyclopropyl) alanine and 3-(trans-2- nitrocyclopropyl) alanine moieties found In the core of belactosln A and hormaomycin, respectively, Is reported. By using an enantioenriched substituted α-nitro diazoester In a diastereoselective Intramolecular cyclopropanatlon reaction, the trans-nitrocyclopropyl alanine moiety can be obtained efficiently In five steps from the Initial α-nitrocyclopropyl lactone unit, thus achieving the synthesis of the cyclopropane core of the two natural products.
Total synthesis of the mycolactones.
Song, Fengbin,Fidanze, Steve,Benowitz, Andrew B,Kishi, Yoshito
, p. 647 - 650 (2002)
[structure: see text] The first total synthesis of the mycolactones is reported. This work unambiguously confirms our earlier relative and absolute stereochemical assignment of the mycolactones.
Technical production of aldehydes by continuous bleach oxidation of alcohols catalyzed by 4-hydroxy-TEMPO
Fritz-Langhals, Elke
, p. 577 - 582 (2005)
Aldehydes can be easily prepared from the corresponding alcohols in good to excellent yields by oxidation with technical bleach and catalytic amounts of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (1b, 4-hydroxy TEMPO, "HOT"). Whereas the well-known batch process performed on lab scale is not suitable for the technical synthesis especially of activated β-substituted aldehydes, this transformation can be performed continuously in a simple tube reactor. This layout meets all requirements necessary for the process, i.e., turbulent mixing of the biphasic mixture, removal of heat, short contact times, and high output. Thus, a single tube of 3 mm diameter renders about 60 mol of aldehyde per day.
A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams
Han, Seo-Jung,Stoltz, Brian M.
, p. 2233 - 2235 (2016)
A straightforward approach toward enantioenriched α-substituted α,β-unsaturated δ-lactams is described. Although a considerable number of approaches toward α,β-unsaturated δ-lactams have been reported, there are relatively few examples of enantioenriched α,δ-disubstituted α,β-unsaturated δ-lactams formation. The δ-stereocenter was formed by addition of allylmagnesium bromide to an N-tert-butylsulfinyl imine. The α,β-unsaturated δ-lactam was furnished by ring-closing metathesis. Although Baylis-Hillman chemistry failed on this cyclic compound, introduction of the hydroxyethyl group prior to ring-closing metathesis was successful. A Baylis-Hillman reaction was used to introduce the substituent at the α-position of the α,β-unsaturated lactam.
