cas 112837-17-9, (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE

Articles about 112837-17-9Total 10 be found

Total synthesis of branimycin: An evolutionary approach
The first total synthesis of the macrolactone antibiotic branimycin (4) has been described. The key disconnection leads to a cis-dehydrodecalone core and a polyketide side chain which are connected via organometallic addition. The dehydrodecalone core was targeted via altogether five different approaches featuring various kinds of chiral elements and ring-closing methodology. In the end the most successful method starting from diepoxynaphthalene 109 was chosen to carry on with the synthesis. Thus the oxygen functions and carbon appendages were introduced via organometallic desymmetrization reactions to generate epoxy ketone 107, to which vinyl iodide 11 was added after conversion into the organolithium species. The synthesis was completed by introducing the ester side chain via Michael addition and subsequent macrolactonization. Competitive approach: The first total synthesis of the macrolactone antibiotic branimycin is described (see figure). The dehydrodecalin core was targeted via five competing approaches featuring various kinds of chiral elements and ring-closing methodology. In this "Darwinian" struggle the most successful route emerged and led to the completion of the synthesis. Copyright
Enev, Valentin S.,Felzmann, Wolfgang,Gromov, Alexey,Marchart, Stefan,Mulzer, Johann
supporting information; experimental part
p. 9651 - 9668
(2012/09/21)

A pyrrolysine analogue for protein click chemistry
(Chemical Equation Presented) Ignoring the STOP sign: A pyrrolysine analogue bearing a terminal alkyne was site-specifically incorporated into recombinant calmodulin (CaM) through a UAG codon. The resulting protein was labeled with an azide-containing dye using a copper(I)-catalyzed click reaction. Subsequent application of an orthogonal cysteine tagging method yielded a CaM labeled with two distinct fluorophores that enabled its study by FRET spectroscopy.
Fekner, Tomasz,Li, Xin,Lee, Marianne M.,Chan, Michael K.
supporting information; experimental part
p. 1633 - 1635
(2009/06/30)

Convenient new syntheses of R-(+)-5-benzyloxymethyl-5H-furan-2-one- a building block en route to L-nucleosides
R-(+)-5-Benzyloxymethyl-5H-furan-2-one (R-(1)) was obtained from commercially available R-(-)-2-benzyloxymethyl oxirane (R-(2)) in two and three steps, respectively. Key steps are a) the nucleophilic ring opening of the oxirane moiety with dianions derived from either PhSeCH2CO2H or PhSCH2CO2H; b) oxidation to the corresponding 1-oxides and c) concomitant or thermally induced syn-elimination. R-(1) was obtained with ≥97% ee and ≥95% ee, respectively.
Fazio, Fabio,Maliakal, Davis,Schneider, Manfred P.
p. 1323 - 1328
(2007/10/03)

A novel synthesis of 2-deoxy-L-ribose
We report a new synthesis of 2-deoxy-L-ribose starting from the commercially available (R)-(+)-5-hydroxymethyl-5H-furan-2-one. The key step is a 1,4-addition of (PhMe2Si)2Cu(CN)Li2 which proceeds with complete diastereoselection. Copyright (C) 2000 Elsevier Science Ltd.
Fazio, Fabio,Schneider, Manfred P.
p. 1869 - 1876
(2007/10/03)

Synthetic study on gymnodimine: Highly stereoselective construction of substituted tetrahydrofuran and cyclohexene moieties
The synthetic studies on gymnodimine, a shellfish toxin, are described. This marine toxin consists of 16-membered carbocycle, tetrahydrofuran, and spiro-imine moieties. Our synthetic strategy involves the stereoselective allylation of tetrahydrofuran compound and the exo-selective intramolecular Diels-Alder reaction.
Ishihara, Jun,Miyakawa, Jun,Tsujimoto, Takashi,Murai, Akio
p. 1417 - 1419
(2007/10/03)

Synthesis of novel L-series 2',3'-dideoxy-3'-hydroxy-methyl-nucleosides and a convenient method for the separation of nucleoside anomers
Photoinduced addition of methanol to 5(R)-(tert- butyldimethylsilyloxymethyl) -2(5H)-furan-2-one (derived from L-gulono-1,4- lactone) provided the photoadduct 5(R)-(tert-butyldimethylsiloxymethyl)- 4(S)-hydroxymethyl-tetrahydrofuran-2-one, which was converted into two L- series-2',3'-dideoxy-3'-hydroxymethyl-nucleosides. In addition, we describe a new method for the chromatographic separation of cytidine anomers using a N- 2-(4-nitrophenyl)ethyl carbamate derivative.
Gould, Jayne H.M.,Mann, John
p. 193 - 213
(2007/10/03)

Synthesis of Optically Active Butenolides and γ-Lactones by the Sharpless Asymmetric Dihydroxylation of β,γ-Unsaturated Carboxylic Esters
Keywords: asymmetric synthesis; butenolides; dihydroxylations; furanones; lactones
Harcken, Christian,Brueckner, Reinhard
p. 2750 - 2752
(2007/10/03)

Lipase-mediated preparation of optically pure four-carbon di- and triols from a meso-precursor
An expedient route to optically pure four-carbon di- and triols, prepared from a meso-symmetric four-carbon precursor by employing lipase-mediated kinetic resolution as a key step.
Yamada,Ogasawara
p. 1291 - 1294
(2007/10/02)

SYNTHESIS OF THE ENANTIOMERS OF UMBELACTONE. CONFIGURATIONAL ASSIGNMENT OF THE NATURAL PRODUCT.
Both (+)- and (-)-umbelactone have been synthetized from (R)-γ-hydroxymethyl-γ-butyrolactone and D-ribonolactone, respectively.The absolute configuration of the natural product has shown to be R-(+).
Ortuno, Rosa M.,Bigorra, Joaquim,Font, Josep
p. 2199 - 2202
(2007/10/02)