105122-15-4Relevant articles and documents
Catalytic ferrier rearrangement of unsaturated nucleosides
Linker, Torsten,Sommermann, Thomas,Gimisis, Thanasis,Chatgilialoglu, Chryssostomos
, p. 9637 - 9638 (1998)
The attempted intermolecular addition of malonyl radicals to 1',2'- unsaturated nucleosides has led to the unexpected formation of furanones. Thus, only catalytic amounts of ceric(IV) ammonium nitrate (CAN), induce a Ferrier rearrangement. The unsaturated lactone was isolated in good yield and can serve as a precursor for the synthesis of optically active products.
Unconventional Fragment Usage Enables a Concise Total Synthesis of (-)-Callyspongiolide
Manoni, Francesco,Rumo, Corentin,Li, Liubo,Harran, Patrick G.
, p. 1280 - 1284 (2018)
An asymmetric synthesis of (-)-callyspongiolide is described. The route builds the macrolide domain atypically from a disaccharide and a monoterpene without passing through a seco-acid. Chiral iridium catalysis selectively joins fragments. Subsequent degradation of an imbedded butyrolactone via perhemiketal fragmentation affords a stereo- and regio-defined homoallylic alcohol that is engaged directly in a carbonylative macrolactonization. Further elaboration of the polyunsaturated appendage provides the natural product in a particularly direct and flexible manner.
Synthesis and antiviral activity of the cyclopropano homolog of 2,3- didehydro-2,3-dideoxythymidine
Sard
, p. 2321 - 2328 (1994)
2,3-Didehydro-2,3-dideoxythymidine is among the nucleoside analogs which have been shown to be clinically useful as anti-HIV agents. Its 2,3- cyclopropano analog has now been synthesized and evaluated. However, the title compound is inactive against HIV.
A domino ring-closing metathesis as a key-step in the synthesis of chiral lactones from D-mannitol
Nay, Bastien,Gaboriaud-Kolar, Nicolas,Bodo, Bernard
, p. 3867 - 3870 (2005)
Chiral lactones were synthesized in six steps from D-mannitol. The key-step was a domino ring-closing metathesis reaction leading to the symmetric cleavage of a D-mannitol triene derivative and to the formation of two molecules of the desired lactone.
A facile entry to bicyclic systems from L-glutamic acid
Frieman, Bryan A.,Bock, Charles W.,Bhat, Krishna L.
, p. 2099 - 2108 (2001)
An efficient synthesis of bicyclic heterocycles has been realized from L-glutamic acid. The key step is the construction of the pyrrole ring in a single step, using tosylmethyl isocyanide (TosMIC) methodology. Structures of reaction intermediates and final products were investigated using density functional theory calculations.
AN EFFICIENT TOTAL SYNTHESIS OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT) AND 3'-AZIDO-2',3'-DIDEOXYURIDINE (AZDDU, CS-87) FROM D-MANNITOL
Chu, Chung K.,Beach, J. Warren,Ullas, Giliyar V.,Kosugi, Yoshiyuki
, p. 5349 - 5352 (1988)
An efficient stereoselective total synthesis of 3'-azido-3'deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZDDU, CS-87) from readily available and inexpensive starting material, D-mannitol has been achieved.
The use of d-mannitol-derived C2-symmetric trienes in tandem metathesis reactions towards valuable lactones
Riache, Nassima,Blond, Alain,Nay, Bastien
, p. 10853 - 10859 (2008)
Chiral lactones were synthesized from d-mannitol. C2-symmetric triene precursors were constructed with a central relay-olefin allowing the key domino ring-closing metathesis to be achieved. It led to the symmetrical cleavage of the substrate and to the formation of 2 mol of the desired 5- or 6-membered lactone. Attempts to form 7-membered lactones thus far only led to 14-membered macrodiolides instead.
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
, p. 1600 - 1604 (2019)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
Process for Preparing Beraprost Intermediate
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Paragraph 0160; 0161, (2018/01/05)
The present invention relates to a method of producing an intermediate necessary for the production of 314d isomer of beraprost in a high yield and in mild reaction conditions. According to the present invention, the method can produce a compound of chemical formula 3 in a high yield, which is a major intermediate necessary for the production of 314d isomer of beraprost, in mild reaction conditions.COPYRIGHT KIPO 2017
Cycloaddition and one-carbon homologation studies in the synthesis of advanced iridoid precursors
Stevens, Anne T.,Caira, Mino R.,Bull, James R.,Chibale, Kelly
supporting information; experimental part, p. 3527 - 3536 (2010/01/06)
A Diels-Alder cycloaddition approach to the sweroside aglycone intermediate of iridoids was explored using silylated butenolides and levoglucosenone as dienophiles under both Lewis acid and thermal conditions. Results of this study reveal no evidence that
