Document Detail


First total synthesis of (5Z,9Z)-(+/-)-2-methoxy-5,9-octadecadienoic acid, a marine derived methoxylated analog of taxoleic acid.
MedLine Citation:
PMID:  18761005     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The first total synthesis for the sponge derived (5Z,9Z)-(+/-)-2-methoxy-5,9-octadecadienoic acid, an analog of taxoleic acid, was accomplished in seven steps and in a 10% overall yield. It was again corroborated that the best strategy to prepare these cis,cis dimethylene interrupted double bonds is the double-alkyne bromide coupling reaction of 1,5-hexadiyne, which provides the advantage of achieving a 100% cis stereochemical purity for both double bonds after hydrogenation under Lindlar conditions. The alpha-methoxy functionality was best prepared via the Mukaiyama reaction of (4Z,8Z)-heptadecadienal with trimethylsilyl cyanide and triethylamine followed by acid hydrolysis. Selective methylation of the hydroxyl group of (5Z,9Z)-(+/-)-2-hydroxy-5,9-octadecadienoic acid was achieved with sodium hydride/methyl iodide when tetrahydrofuran was used as solvent. Complete spectral data is presented, for the first time, for this unusual marine alpha-methoxylated fatty acid.
Authors:
Néstor M Carballeira; Rosann O'Neill; Diana Silva
Related Documents :
17291005 - Dynamic kinetic resolution of primary amines with a recyclable pd nanocatalyst for race...
16671775 - A concise, enantioselective approach to (-)-quinic acid.
19465645 - Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond.
21869955 - Extraction and isolation of shikimic acid from ginkgo biloba leaves utilizing an ionic ...
1376755 - Simple assays of retinoid activity as potential screens for compounds that may be usefu...
19274595 - Analysis of constituents of metal elements and amino acids in new cultivar citrus retic...
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2008-08-08
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  156     ISSN:  1873-2941     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2008 Nov 
Date Detail:
Created Date:  2008-11-10     Completed Date:  2009-01-19     Revised Date:  2014-09-22    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  41-4     Citation Subset:  IM    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Animals
Esterification
Fatty Acids, Unsaturated / chemical synthesis*,  chemistry
Furans / chemistry
Porifera / chemistry
Stearic Acids / chemical synthesis*,  chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
S06 GM08102/GM/NIGMS NIH HHS; SC1 GM084708/GM/NIGMS NIH HHS; SC1 GM084708-01/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/2-methoxy-5,9-octadecadienoic acid; 0/Fatty Acids, Unsaturated; 0/Furans; 0/Stearic Acids; 3N8FZZ6PY4/tetrahydrofuran
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Expression of methyl CpG binding protein 2 (Mecp2) during the postnatal development of the mouse bra...
Next Document:  Cryopreserved peripheral blood mononuclear cells are suitable for the assessment of immunological ma...