82010-51-3Relevant academic research and scientific papers
DIASTEREO- AND ENANTIOSELECTIVE REDUCTION OF α,β-DIKETODITHIANE WITH THE BAKER'S YEAST
Fujisawa, Tamotsu,Kojima, Eiji,Itoh, Toshiyuki,Sato, Toshio
, p. 6089 - 6092 (1985)
The Baker's yeast reduction of 1-(1,3-dithian-2-yl)-1,2-propanedione gave highly enantio- and diastereoselectively (S)-(+)-1-(1,3-dithian-2-yl)-2-hydroxy-1-propanone or (1S,2S)-(+)-1-(1,3-dithian-2-yl)-1,2-propanediol, depending on the reaction time.The hydroxy ketone was reduced with diisobutylaluminum hydride to give (1R,2S)-1-(1,3-dithian-2-yl)-1,2-propanediol with high diastereoselectivity.The former (1S,2S)-diol was converted into L-digitoxose.
Versicolactones A and B: Total synthesis and structure revision
Wang, Liping,Zhu, Weiming
supporting information, p. 6729 - 6731 (2013/11/19)
To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The 1H and 13C NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta- 2,4-dien-4-lactone, respectively.
Synthesis and structure of diastereomers of pentenocin B produced by Trichoderma hamatum FO-6903
Ohira, Susumu,Fujiwara, Hiroyuki,Maeda, Kiyomi,Habara, Masaharu,Sakaedani, Naomi,Akiyama, Megumi,Kuboki, Atsuhito
, p. 1639 - 1641 (2007/10/03)
All diastereomers of pentenocin B, an inhibitor of interleukin-1β converting enzyme produced by Trichoderma hamatum FO-6903, were synthesized in chiral forms starting from L-threonine. Absolute configurations of natural pentenocin B were clarified to be 4S, 5R, and 6R.
A Simple Synthesis of all four Stereoisomers of 2,2,5-Trimethyl-1,3-dioxolane-4-carbaldehyde
Binder, W. H.,Prenner, R. H.,Schmid, W.
, p. 763 - 772 (2007/10/02)
A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed.Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage.This procedure allows an application on a multigram scale. - Keywords. 2,2,5-Trimethyl-1,3-dioxolane-4-carbaldehydes, aldopentose diethyl dithioacetals, lead tetraacetate cleavage.
Synthesis of (-)-Biopterin Using (S)-Ethyl Lactate as a Starting Material
Kikuchi, Haruhiko,Mori, Kenji
, p. 2095 - 2100 (2007/10/02)
(-)-Biopterin was synthesized from (1S,2S)-1-(1,3-dithian-2-yl)propane-1,2-diol 5 (=C), which was derived from commercially available (S)-ethyl lactate.Diol 5 (=C) was converted to 15 through a six-step sequence.Ketone 15 was submitted to condensation with 3,5,6-triaminopyrimidinol (TAP, 2), and followed by oxidation to afford isopropylidenebiopterin (16).Finally, 16 was deprotected to give (-)-biopterin (1).
STEREOSELECTIVE CONDENSATION OF BIS-p-TOLYLTHIOMETHANE WITH LACTIC ACID DERIVATIVES THROUGH AN ACYLATION-REDUCTION STRATEGY: SYNTHESIS OF PROTECTED 4-DEOXY-L-THREOSE AND 4-DEOXY-L-ERYTHROSE
Guanti, Giuseppe,Banfi, Luca,Guaragna, Alberto,Narisano, Enrica
, p. 2369 - 2376 (2007/10/02)
The condensation of lithium bis-p-tolylthiomethanide with protected ethyl-L-lactates gave a series of 3-alkoxy- (or 3-hydroxy-) 1,1-bis-p-tolylthiobutan-2-ones, which were stereoselectively reduced to the corresponding syn- or anti-alcohols with diastereo
Molecular and Crystal Structure of Hyptolide, a Naturally Occurring α,β-Unsaturated δ-Lactone
Achmad, Sjamsul,Hoeyer, Thomas,Kjaer, Anders,Makmur, Lukman,Norrestam, Rolf
, p. 599 - 609 (2007/10/02)
Hyptolide, a six-membered, α,β-unsaturated C12 lactone, has been reisolated from Hyptis pectinata Poit.Detailed 1H and 13C NMR spectroscopic studies and a crystal structure determination on the basis of single-crystal X-ray diffraction data collected at 293 K provide evidence for the detailed structure and relative configuration of hyptolide.The crystal structure has been determined from 2261 most significant X-ray intensities and refined to an R factor of 0.065.The space group is P21 and the cell parameters are a = 7.629(2), b = 24.639(3), c = 10.468(2) Angstroem and β = 90.64(2) deg.The absolute configuration is established by synthesis of 10(S),11(R)-dihydroxydodecanoic acid, the enantiomer of an acid previously produced by exhaustive hydrogenation of hyptolide.On the basis of the combined evidence, supported by chiroptical data, hyptolide can now be formulated as 6R-(1Z,3S,5R,6S)-5,6-dihydro-6--2H-pyran-2-one.Its relation to other C12-lactones of natural origin is briefly discussed.
Enantiospecific Synthesis of Protected 4-Deoxy-L-threose and 4-Deoxy-L-erythrose via Diastereoselective Reduction of L-Lactic Acid-derived Ketones
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 136 - 138 (2007/10/02)
The title compounds were synthesized from L-lactic acid via an acylation-reduction sequence employing lithium bis-p-tolylthiomethanide as a formyl anion equivalent.
Synthesis of N-Trifluoroacetyl-L-acosamine and -L-daunosamine
Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero
, p. 442 - 444 (2007/10/02)
N-Trifluoroacetyl-L-acosamine (18) has been chirally synthesised from the chiral educt (1) obtained from cinnamaldehyde and bakers' yeast, whereas N-trifluoroacetyl-L-daunosamine (17) was obtained by inverting the configuration at C-4 of the intermediate
