130412-79-2Relevant academic research and scientific papers
Stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue
Dong, Guang Ri,Hong, Seungmin,Kim, Seung In,Kim, In Su,Jung, Young Hoon
experimental part, p. 4200 - 4205 (2012/10/07)
The stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue was achieved from readily available D-erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2-anti-dibenzyl ether to afford the 1,2-anti-amino alcohol. The total synthesis of (-)-α-conhydrine and its pyrrolidine analogue starting from readily available D-erythronolactone was achieved via the regioselective and diastereoselective allylic amination of anti-1,2-dibenzyl ether by using chlorosulfonyl isocyanate.
An unexpected high erythro-selection in the Grignard reaction with an N,O-acetal: A concise asymmetric synthesis of indolizidine alkaloid (-)-2-epi-lentiginosine
Zhuang, Jia-Jia,Ye, Jian-Liang,Zhang, Hong-Kui,Huang, Pei-Qiang
experimental part, p. 1750 - 1755 (2012/03/10)
Starting from commercially available lactone 10, a concise and highly diastereoselective synthesis of (-)-(lS,2R,8aS)-2-epi-lentiginosine (2) is described. The synthesis featured an unexpected highly erythro-selective reaction of Grignard reagent 7 with the protected N,O-acetal 8. The stereochemical outcome of this reaction is contrary to the known results involving the reactions with O-benzyl protected aminofuranosides and aminoglycosides. Thus, this method constitutes an extension of the threo-diastereoselective C-C bond formation methodology.
Synthesis of (-)-swainsonine and (-)-8epi-swainsonine by the addition of allenylmetals to chiral α,β-alkoxy sulfinylimines
Louvel, Julien,Chemla, Fabrice,Demont, Emmanuel,Ferreira, Franck,Perez-Luna, Alejandro
supporting information; experimental part, p. 6452 - 6455 (2012/01/15)
The asymmetric synthesis of (-)-swainsonine and (-)-8epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl] trimethylsilane to enantiopure α,β-dialkoxy N-tert- butanesulfinylimines derived from Derythronolactone.
A simple route for synthesis of 4-phospho-D-erythronate
Novikov, Yehor,Copley, Shelley D.,Eaton, Bruce E.
supporting information; experimental part, p. 1913 - 1915 (2011/04/22)
4-Phospho-d-erythronate is an intermediate in the synthesis of pyridoxal 5′-phosphate in some bacteria and an inhibitor of ribose 5-phosphate isomerase. Previous synthetic schemes for the preparation of 4-phospho-d-erythronate required expensive precursors and typically gave low yields. We report a straightforward synthesis of 4-phospho-d-erythronate from the inexpensive precursor d-erythronolactone in five steps with a preparatively useful yield of 22%.
Design and synthesis of substrate and intermediate analogue inhibitors of S-ribosylhomocysteinase
Shen, Gang,Rajan, Rakhi,Zhu, Jinge,Bell, Charles E.,Pei, Dehua
, p. 3003 - 3011 (2007/10/03)
S-Ribosylhomocysteinase (LuxS) catalyzes the cleavage of the thioether linkage in S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione, the precursor of autoinducer 2. Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. LuxS utilizes a divalent metal ion as a Lewis acid during catalysis. In this work, a series of structural analogues of the substrate SRH and a 2-ketone intermediate were designed and synthesized. Kinetic studies indicate that the compounds act as reversible, competitive inhibitors against LuxS, with the most potent inhibitors having K1 values in the submicromolar range. These represent the most potent LuxS inhibitors that have been reported to date. Cocrystal structures of LuxS bound with two of the inhibitors largely confirmed the design principles, i.e., the importance of both the homocysteine and ribose moieties in high-affinity binding to the LuxS active site.
(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets
Smith III, Amos B.,Fox, Richard J.,Vanecko, John A.
, p. 3099 - 3102 (2007/10/03)
(Chemical Equation Presented) Effective stereocontrolled syntheses of subtargets (-)-2 and (-)-4, comprising respectively the C(16-29) and C(1-15) tetrahydropyran and dihydropyran moieties of the potent antibiotic (+)-sorangicin A (1), have been achieved. The cornerstone for the synthesis of (-)-2 involved an aldol tactic exploiting 1,4-induction, followed in turn by an acid-mediated cyclization/ketalization and hydrosilane reduction promoted by TMSOTf, while construction of (-)-4 entailed a stereoselective conjugate addition/α-oxygenation sequence.
Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes
Marshall, James A.,Seletsky, Boris M.,Luke, George P.
, p. 3413 - 3420 (2007/10/02)
Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.
