89291-76-9Relevant academic research and scientific papers
Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase
Jeong, Lak Shin,Yoo, Su Jeong,Lee, Kang Man,Koo, Mi Jeong,Choi, Won Jun,Kim, Hea Ok,Moon, Hyung Ryong,Lee, Min Young,Park, Jae Gyu,Lee, Sang Kook,Chun, Moon Woo
, p. 201 - 203 (2007/10/03)
Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanoc
First synthesis of (-)-neplanocin C
Comin, María J.,Rodriguez, Juan B.
, p. 4639 - 4649 (2007/10/03)
(-)-Neplanocin C (4), a minor component of the neplanocin family of antibiotics and a lead drug for the design of several conformationally constrained nucleosides analogues, was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in twelve steps. The proton NMR spectrum of 4 was in agreement with the corresponding natural product. Calculated coupling constants obtained from ab initio molecular modeling studies and from previously published X-ray structure of neplanocin C also corresponded to the spectroscopic data. (C) 2000 Elsevier Science Ltd.
Chiral pool synthesis of 4a-substituted carbocyclic cyclopentanoid nucleoside precursors, I
Csuk, Rene,Doerr, Petra,Kuehn, Martin,Krieger, Claus,Antipin, Mikhael Y.
, p. 1068 - 1078 (2007/10/03)
A suitable protected D-ribono-1,4-lactone derivative has been used for the straightforward chiral pool synthesis of cyclopentanoid nucleoside precursors. Thus, epoxidation followed by deoxygenation or regioselective ring opening led to nucleoside precurso
Synthesis and anti-HIV activity of carbocyclic ring-enlarged 4′,1′a-methano oxetanocin analogues
Jeong, Lak S.,Bae, Min,Chun, Moon W.,Marquez, Victor E.
, p. 1059 - 1062 (2007/10/03)
Synthesis of carbocyclic ring-enlarged 4′,1′a-methano oxetanocin analogues via completely regioselective opening of cyclic sulfites by sodium azide or purine bases is described. Copyright
TOTAL SYNTHESIS OF (+/-)-NEPLANOCIN F
Bodenteich, Michael,Marquez, Victor E.
, p. 4909 - 4912 (2007/10/02)
(+/-)-Neplanocin F was synthesized in 12 steps from the racemate (3/4), which was available from D-ribonolactone.
Total Synthesis of (-)-Neplanocin A
Marquez, Victor E.,Lim, Mu-Ill,Tseng, Christopher K.-H.,Markovac, Anica,Priest, Matthew A.,et al.
, p. 5709 - 5714 (2007/10/02)
An efficient synthesis of neplanocin A, which is easily adaptable for the preparation of other cyclopentenyl containing nucleoside isosteres, has been developed.This enantioselective synthesis provides control of two of the three chiral centers of neplano
SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDE (-)-NEPLANOCIN A
Medich, John R.,Kunnen, Kevin B.,Johnson, Carl R.
, p. 4131 - 4134 (2007/10/02)
(-)-Neplanocin A has been prepared in 14 steps from cyclopentadiene (11percent overall yield).
TOTAL SYNTHESIS OF (-)-NEPLANOCIN A
Lim, Mu-ill,Marquez, Victor E.
, p. 5559 - 5562 (2007/10/02)
A total synthesis of (-)-neplanocin A has been accomplished in 15 steps starting from the readily available D-(+)-ribonic acid γ-lactone.
