A New Formal Synthetic Route to Entecavir

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 748-752
Author(s):  
Xiaoji Wang ◽  
Shuangping Huang ◽  
Lixia Liu ◽  
Yongli Sun ◽  
Jiwu Wang ◽  
...  
Keyword(s):  
Hepatitis B ◽  
Selenium Dioxide ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Virus Inhibitor ◽  
B Virus ◽  
Epoxide Opening ◽  
Key Features ◽  
Sharpless Asymmetric Epoxidation ◽  
Straightforward Approach

We describe a new and straightforward approach to the formal synthesis of the hepatitis B virus inhibitor entecavir, an important hepatitis B drug, in ten steps overall. Key features of the route are a Morita–Baylis–Hillman reaction, a Sharpless asymmetric epoxidation, a reductive epoxide opening of an α,β-epoxy ketone, and a Riley selenium dioxide oxidation.

Stereo-Controlled Total Synthesis of Ieodomycins A and B

2014 ◽  
Vol 881-883 ◽  
pp. 57-60 ◽  
Author(s):  
Cheng Lin Zhu ◽  
Jian Ting Zhang ◽  
Shi Peng Chen ◽  
Jun Min Feng ◽  
Gao Peng Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Aldol Reaction ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Mukaiyama Aldol ◽  
Synthetic Sequence ◽  
Key Features ◽  
Swern Oxidation ◽  
Sharpless Asymmetric Epoxidation

A highly convergent formal synthesis of Ieodomycins A and B was achieved in 7 steps. The key features involved in the synthetic sequence of Ieodomycins A and B are the Sharpless asymmetric epoxidation and the Mukaiyama aldol reaction[. The synthesis of C-3 epimer of Ieodomycins A and B was also accomplished in good yields, but now just Heptyl diene aldehyde was getted thought 4 steps. Use Geraniol as meterials to make the corresponding aldehyde (1) via Swern oxidation. Though epoxidation, Wittig reaction and HIO4oxidation to get the intermediate . Useing it though few steps, the target molecule can be getted.

Effect of a hepatitis B virus inhibitor, NZ-4, on capsid formation

2016 ◽  
Vol 125 ◽  
pp. 25-33 ◽  
Author(s):  
Li Yang ◽  
Ya-Juan Wang ◽  
Hai-Jun Chen ◽  
Li-Ping Shi ◽  
Xian-Kun Tong ◽  
...  
Keyword(s):  
Hepatitis B Virus ◽  
Hepatitis B ◽  
Virus Inhibitor ◽  
Capsid Formation ◽  
B Virus

scholarly journals Screening for inhibitor of episomal DNA identified dicumarol as a hepatitis B virus inhibitor

PLoS ONE ◽  
2019 ◽  
Vol 14 (2) ◽  
pp. e0212233 ◽  
Author(s):  
Fumihiko Takeuchi ◽  
Sotaro Ikeda ◽  
Yuta Tsukamoto ◽  
Yoshikazu Iwasawa ◽  
Chen Qihao ◽  
...  
Keyword(s):  
Hepatitis B Virus ◽  
Hepatitis B ◽  
Virus Inhibitor ◽  
B Virus ◽  
Episomal Dna

scholarly journals Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments­ of Macrolactin 3

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0166-0172
Author(s):  
A. Maheshwar Reddy ◽  
Gowravaram Sabitha
Keyword(s):  
Double Bond ◽  
Michael Addition ◽  
Asymmetric Epoxidation ◽  
Efficient Synthesis ◽  
Stereogenic Centers ◽  
Epoxide Opening ◽  
Diene System ◽  
Sharpless Asymmetric Epoxidation

We describe herein an efficient synthesis of the C1–C9, C11–C19 pyran moiety and C18–C24 core fragments of macrolactin 3. The prominent features of this work include construction of the Z-double bond of the 1,3-(Z,E)-diene system utilizing Horner–Wadsworth–Emmons­ reaction under Still–Gennari conditions. A Sharpless asymmetric epoxidation and subsequent epoxide opening under BF3·OEt2 conditions were applied to generate the stereogenic centers at C15 and C16, oxa-Michael addition and Jacobsen resolution facilitate the synthesis of the fragments.

First Total Synthesis of Jomthonic Acid A

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 69-72
Author(s):  
Mohan Dumpala ◽  
Batthula Srinivas ◽  
Palakodety Radha Krishna
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Asymmetric Epoxidation ◽  
Synthetic Strategy ◽  
Amide Coupling ◽  
Key Features ◽  
Sharpless Asymmetric Epoxidation

A stereoselective total synthesis of jomthonic acid A is described. The key features of the synthetic strategy are a Sharpless asymmetric epoxidation, a Gilmann reagent-induced methylation, a Mitsunobu reaction, a Yamaguchi esterification, and an O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU)-mediated amide coupling. Jomthonic acid A is an architecturally rare amino acid containing a β-methylphenylalanine residue and a 4-methyl-(2E,4E)-hexa-2,4-dienoate moiety. It shows antidiabetic and antiatherogenic activities when tested against mouse ST-13 preadiopocytes.

Precore hepatitis B virus carrying lamivudine resistant mutations are not associated with decreassed replication fitness and are sensitive to adefovir

2001 ◽  
Vol 120 (5) ◽  
pp. A64-A64
Author(s):  
R CHEN ◽  
P DESMOND ◽  
W DELANEY ◽  
D COLLEDGE ◽  
R EDWARDS ◽  
...  
Keyword(s):  
Hepatitis B Virus ◽  
Hepatitis B ◽  
B Virus ◽  
Replication Fitness

Hepatifis B virus kinetics in acute hepatitis B-A comparison between lamivudine-treated and -untreated case

2001 ◽  
Vol 120 (5) ◽  
pp. A385-A385
Author(s):  
K MICHITAKA ◽  
K KAWAI ◽  
H MATSUBARA ◽  
S NAKANISHI ◽  
N HORIIKE ◽  
...  
Keyword(s):  
Hepatitis B ◽  
Acute Hepatitis ◽  
Untreated Case ◽  
B Virus ◽  
Acute Hepatitis B

Prevalence and Clinical Implications of Hepatitis B Virus Genotypes in Southern Taiwan

2003 ◽  
Vol 38 (1) ◽  
pp. 95-101 ◽  
Author(s):  
Lee C.-M. ◽  
Chen C.-H. ◽  
Lu S.-N. ◽  
Tung H.-D. ◽  
Chou W.-J. ◽  
...  
Keyword(s):  
Hepatitis B Virus ◽  
Hepatitis B ◽  
Clinical Implications ◽  
B Virus ◽  
Virus Genotypes ◽  
Southern Taiwan
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