- Total synthesis of uradl polyoxin c
-
An improved synthesis of methyl (methyl 5-azido-5deoxy-2,3-O-isopropylidene-β-D-allofuranosid)uronate (7) from methyl 2,3-0-isopropylidene-β-D-rifro-pentodialdo-l,4-furanoside (6), using vinylmagnesium bromide in the key step, and its application to the total synthesis of uracil polyoxin C (1) are described.
- Kato, Keisuke,Chen, Cheng Yu,Akita, Hiroyuki
-
p. 1527 - 1533
(2007/10/03)
-
- (1-Ethoxyvinyl)lithium in the total synthesis of thymine polyoxin C and uracil polyoxin C
-
A short path synthesis of the ethyl (methyl 2,3-O-isopropylidene-β-D- allofuranosid)uronate (5) and ethyl (methyl 2,3-O-isopropylidene-α-L- talofuranosid)uronate (6) from methyl 2,3-O-isopropylidene-β-D- ribopentodialdo-1,4-furanoside (3) using (1-ethoxyvinyl)lithium and its application to the total synthesis of the pyrimidine nucleosides, thymine polyoxin C (1) and uracil polyoxin C (2), are described.
- Akita, Hiroyuki,Uchida, Kimio,Chen, Cheng Yu.,Kato, Keisuke
-
p. 1034 - 1038
(2007/10/03)
-
- A short path synthesis of α-hydroxy ester from aldehyde using (1-ethoxyvinyl)lithium and its application to the syntheses of thymine polyoxin c and uracil polyoxin C
-
A short path synthesis of the α-hydroxy esters (4 and 5) from the aldehyde (3) using (1-cthoxyvinyl)lithium and its application to the total syntheses of the pyrimidine nucleoside, thymine polyoxin C (1) and uracil polyoxin C (2), are described.
- Akita, Hiroyuki,Uchida, Kimio,Chen, Cheng Yu
-
-
- Synthesis of uracil polyoxin C from uridine
-
An improved procedure is reported for the asymmetric synthesis of uracil polyoxin C (UPOC) from 2',3'-O-isopropylideneuridine-5'-aldehyde. The methodology described here is based on the highly diastereocontrolled formation of 1-(β-D-allofuranosyl)uracil a
- Evina, Claude Mvondo,Guillerm, Georges
-
p. 163 - 166
(2007/10/02)
-
- (Phenylthio)nitromethane in the Total Synthesis of Polyoxin C
-
The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described.Condensation of (phenylthio)nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 5 gave the (Z)-nitro olefin 6.Addition of potassium trimethylsilanoate and ozonolysis gave the α-hydroxy thioester 7, which was formed with excellent diastereoselectivity.The alcohol 7 was converted into polyoxin C (1) and uracil polyoxin C (2) via the azide 11 and base incorporation using the Vorbrueggen method.
- Barrett, Anthony G. M.,Lebold, Suzanne A.
-
p. 3853 - 3857
(2007/10/02)
-