13265-84-4Relevant articles and documents
Cesium carbonate-promoted Michael-type addition of thiols to hex-1-en-3-ulose: A practical synthesis of 2-deoxy-1-thio-α-hexopyranosid- 3-ulose template
Ganguly, Debashis,Tang, Haiqun,Rodriguez, Michael J.
, p. 4219 - 4226 (2007)
The template 2-deoxy-1-thio-α-hexopyranosid-3-ulose was synthesized in quantitative yield and high diastereoselectivity by 1,4-addition of aryl and alkyl thiols to hex-1-en-3-ulose promoted by cesium carbonate in THF. Copyright Taylor & Francis Group, LLC
Studies directed toward the total synthesis of Scytophycin C: Synthesis of the C(1)-C(18) fragment of Scytophycin C
Grieco, Paul A.,Speake, Jason D.
, p. 1275 - 1278 (1998)
The synthesis of the C(1) to C(18) fragment of Scytophycin C is described which features a highly stereoselective carbon Ferrier-type reaction in 3.0 M lithium perchlorate/ethyl acetate.
C-glycosides and C-disaccharide precursors through carbonylative stille coupling reactions
Jeanneret, Vincent,Meerpoel, Lieven,Vogel, Pierre
, p. 543 - 546 (1997)
Under CO atmosphere and in the presence of Pd2(dba)3 and Ph3As a suitably protected 1-stannylglucal derivative could be carbonylated and coupled to 5-bromo-7-oxabidyclo[2.2.1]hept-5-en-2-yl derivatives. The carbonylative Stille coupling was also successful between 1-iodoglucals and tributyl(vinyl)stannane or tributyl(fur-2-yl)stannane. A cross-conjugated dienone was also obtained through coupling of a 1-stannylglucal with a 1-iodoglucal derivative.
Syntheses of new bidentate thioethylphosphine ligands and their rhodium (I) complexes with carbohydrates as chiral groups
Borwitzky, Angela,Schareina, Thomas,Paetzold, Eckhard,Oehme, Guenther
, p. 115 - 121 (1996)
Substitution-, addition-and rearrangement reactions on easily available derivatives of carbohydrates (1, 2 and 4) with diphenylvinylphosphine or 2-mercaptoethyldiphenylphosphine gave chiral bidentate β-thioethylphosphine ligands (5-9). These compounds for
A concise, enantioselective synthesis of (+)-decarestrictine L from Tri-O-acetyl-D-glucal
Zuniga, Andrea,Perez, Manuel,Pazos, Gonzalo,Gomez, Generosa,Fall, Yagamare
, p. 2446 - 2450 (2010)
We describe a new and efficient approach to the enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-D-glucal, based on a stereoselective Michael addition. Georg Thieme Verlag Stuttgart · New York.
Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity
Ghosh, Arun K.,Reddy, Guddeti Chandrashekar,Kovela, Satish,Relitti, Nicola,Urabe, Veronica K.,Prichard, Beth E.,Jurica, Melissa S.
, p. 7293 - 7297 (2018)
Spliceostatin A is a potent inhibitor of spliceosomes and exhibits excellent anticancer activity against multiple human cancer cell lines. We describe here the design and synthesis of a stable cyclopropane derivative of spliceostatin A. The synthesis invo
Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester
Ghosh, Arun K.,Reddy, Guddeti Chandrashekar,MacRae, Andrew J.,Jurica, Melissa S.
, p. 96 - 99 (2018)
An enantioselective total synthesis of spliceostatin G has been accomplished. The synthesis involved a Suzuki cross-coupling reaction as a key step. The functionalized tetrahydropyran ring was constructed from commercially available optically active tri-O-acetyl-d-glucal. Other key reactions include a highly stereoselective Claisen rearrangement, a Cu(I)-mediated 1,4 addition of MeLi to install the C8 methyl group, and a reductive amination to incorporate the C10 amine functionality of spliceostatin G. Biological evaluation of synthetic spliceostatin G and its methyl ester revealed that it does not inhibit splicing in vitro.
Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition
Ghosh, Arun K.,Veitschegger, Anne M.,Nie, Shenyou,Relitti, Nicola,Macrae, Andrew J.,Jurica, Melissa S.
, p. 5187 - 5198 (2018)
Thailanstatin A has been isolated recently from the fermentation broth of B. thailandensis MSMB43. We describe here an enantioselective convergent synthesis of thailanstatin A methyl ester and evaluation of its splicing activity. Synthesis of both highly functionalized tetrahydropyran rings were carried out from commercially available tri-O-acetyl-d-glucal as the key starting material. Our convergent synthesis involved the synthesis of both tetrahydropyran fragments in a highly stereoselective manner. The fragments were then coupled using cross-metathesis as the key step. The synthesis of the diene subunit included a highly stereoselective Claisen rearrangement, a Cu(I)-mediated conjugate addition of MeLi to set the C-14 methyl stereochemistry, a reductive amination reaction to install the C16-amine functionality, and a Wittig olefination reaction to incorporate the diene unit. The epoxy alcohol subunit was synthesized by a highly selective anomeric allylation, a Peterson olefination, and a vanadium catalyzed epoxidation that installed the epoxide stereoselectively. Cross-metathesis of the olefins provided the methyl ester derivative of thailanstatin A. We have carried out in vitro splicing studies of the methyl ester derivative, which proved to be a potent inhibitor of the spliceosome.
AN APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE TRICHOTHECENES FROM TRI-O-ACETYL-D-GLUCAL
Fetizon, M.,Khac, Duc Do,Tho, Nguyen Dinh
, p. 1777 - 1780 (1986)
A chiral synthesis of the B-C ring system of trichothecenes from tri-O-acetyl-D-glucal by using a photochemical cycloaddition of acetylene to the unsaturated ketone 7, followed by acid-catalyzed rearrangement, is described.
Some derivatives of 3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (KDN)
David,Malleron,Cavaye
, p. 233 - 241 (1994)
Treatment of a solution of 3-deoxy-D-glycero-D-galacto-non-2-ulosonic (KDN) in 11 N aqueous hydrochloric acid with an excess of ethanethiol gave in 52% yield the diethyl dithioacetal of the corresponding 1,4-lactone, which was further characterized as its peracetate. With 1,3-propanedithiol, only one thiol function reacted and the product, isolated in 18% yield as its peracetate, was a vinyl thioether of the α,β-unsaturated 1,4-lactone. The methyl ester methyl β-glycopyranoside derivative of KDN could be converted to the 8,9-isopropylidene ketal 7 (69%). Conditions were found which allow selective silylation at C-4 with tert-butylchlorodimethylsilane, giving the 4-O-tert-butylsilyl derivative in 91% yield. Heating it with bis(tributyltin) oxide afforded the 1,7-lactone with inversion of the ring conformation. Lithium aluminium hydride reduction of 7 afforded the corresponding methyl non-2-ulopyranoside, which was converted to the 1,4-bis(silyl) ether. Bromination of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol in aqueous solution at 0°C with N-bromophthalimide gave a mixture of bromodeoxy hexoses from which 2-bromo-2-deoxy-D-mannose was isolated in 60% yield by crystallization. Its incubation with pyruvate in the presence of sialyl aldolase gave 5- bromo-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid 16 in 70% yield. Treatment of a solution of 3-deoxy-D-glycero-D-galacto-non-2-ulosonic (KDN) in 11 N aqueous hydrochloric acid with an excess of ethanethiol gave in 52% yield the diethyl dithioacetal of the corresponding 1,4-lactone, which was further characterized as its peracetate. With 1,3-propanedithiol, only one thiol function reacted and the product, isolated in 18% yield as its peracetate, was a vinyl thioether of the α,β-unsaturated 1,4-lactone. The methyl ester methyl β-glycopyranoside derivative of KDN could be converted to the 8,9-isopropylidene ketal 7 (69%). Conditions were found which allow selective silylation at C-4 with tert-butylchlorodimethylsilane, giving the 4-O-tert-butylsilyl derivative in 91% yield. Heating it with bis(tributyltin) oxide afforded the 1,7-lactone with inversion of the ring conformation. Lithium aluminium hydride reduction of 7 afforded the corresponding methyl non-2-ulopyranoside, which was converted to the 1,4-bis(silyl) ether. Bromination of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol in aqueous solution at 0°C with N-bromophthalimide gave a mixture of bromodeoxy hexoses from which 2-bromo-2-deoxy-D-mannose was isolated in 60% yield by crystallization. Its incubation with pyruvate in the presence of sialyl aldolase gave 5-bromo-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid 16 in 70% yield.
