scholarly journals Synthesis of Glucuronic Acid Conjugates of Linoleic Acid Metabolites

2013 ◽  
Vol 57 (6) ◽  
pp. 738-743
Author(s):  
Dong Wook Kang
2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Junzo Nokami ◽  
Kazuhiko Fujii ◽  
Yusuke Mizutani ◽  
Rikiya Omatsu ◽  
Kiyoshi Watanabe ◽  
...  

Linoleic acid metabolites (-)-methyl jasmonate and (+)-12-oxophytodienoic acid ((+)-12-oxo-PDA) were prepared from the same precursor (1,2-trans, 1,3- cis, 2′ Z)-2-(pent-2′-enyl)-cyclopent-4-en-1,3-diol which was obtained by regioselective pent-2-enylation of cyclopentadiene and following photooxidation to cis −1,3-diol. A methoxycarbonylmethyl substituent was introduced to the cyclopentane ring via alkylation of the π-allyl palladium intermediate derived from (1 R,2 S,3 S,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with dimethyl malonate for (-)-methyl jasmonate. The α-chain was introduced to the cyclopentane ring via the SN2 type nucleophilic substitution of (1 S,2 R,3 R,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with a dialkylcuprate for (+)-12-oxo-PDA.


2010 ◽  
Vol 48 (10) ◽  
pp. 1311-1320 ◽  
Author(s):  
Lukas Kubala ◽  
Kara R. Schmelzer ◽  
Anna Klinke ◽  
Hana Kolarova ◽  
Stephan Baldus ◽  
...  

1975 ◽  
Vol 3 (1) ◽  
pp. 188-191
Author(s):  
BRIAN G. LAKE ◽  
RONALD C. LONGLAND ◽  
ROSALYN A. HODGSON ◽  
BRIAN J. SEVERN ◽  
SHARAT D. GANGOLLI ◽  
...  

2012 ◽  
Vol 27 (4) ◽  
pp. 422-432 ◽  
Author(s):  
Zhi-Xin Yuan ◽  
Stanley I. Rapoport ◽  
Steven J. Soldin ◽  
Alan T. Remaley ◽  
Ameer Y. Taha ◽  
...  

2002 ◽  
Vol 2 (3) ◽  
pp. 219-230 ◽  
Author(s):  
Lex A. Mitchell ◽  
David F. Grant ◽  
Russell B. Melchert ◽  
Nathan M. Petty ◽  
Richard H. Kennedy

Sign in / Sign up

Export Citation Format

Share Document