- 1-Nitroicosane as the key building block for the first synthesis of triacontan-11-ol, a new fatty alcohol isolated from Argemone mexicana
-
The first synthesis of triacontan-11-ol, a new fatty alcohol isolated from Argemone mexicana, has been realized starting from the nitroaldol reaction of 1-nitroicosane with decanal. Dehydration of the obtained nitroalkanol gives a long-chain nitroalkene which is then reduced to the corresponding nitroalkane. Nef transformation of the latter produces a ketone that is easily reduced to the fatty alcohol 9 in 21% overall yield. Georg Thieme Verlag Stuttgart.
- Ballini, Roberto,Fiorini, Dennis,Palmieri, Alessandro
-
-
Read Online
- The synthesis of long-chain α-alkyl-β-hydroxy esters using allylic halides in a Frater-Seebach alkylation
-
The Frater-Seebach alkylation is a highly efficient means to diastereoselectively introduce α-substituents to chiral β-hydroxy esters, however, the yields of reactions in which longer chain alkyl halides are used can be disappointing. To provide a more robust protocol for the alkylation of β-hydroxy esters, we prepared a variety of long-chain allylic iodides with the view that the greater reactivity of the allylic system would lead to enhanced efficiency. Indeed, for all substrates studied, the yield of the α-alkylation was greatly improved for the unsaturated allylic halides compared to their analogous saturated counterparts. Our methodology thus provides an improved means by which to access a variety of important lipophilic compounds such as mycolic acids, which are found on the cell wall of M. tuberculosis. An improved methodology for the introduction of α-substituents to chiral β-hydroxy esters using Frater-Seebach methodology is presented. Long-chain allylic iodides resulted in better yields for the α-alkylation compared to their saturated counterparts. This methodology provides an improved means by which to access a variety of important lipophilic compounds such as mycolic acids. Copyright
- Khan, Ashna A.,Chee, Stephanie H.,Stocker, Bridget L.,Timmer, Mattie S. M.
-
supporting information; experimental part
p. 995 - 1002
(2012/03/27)
-
- The fluid-mosaic model, homeoviscous adaptation, and ionic liquids: Dramatic lowering of the melting point by side-chain unsaturation
-
(Figure Presented) Defying conventional wisdom: Ionic liquids (ILs) with long, unsaturated alkyl appendages (see top structure) defy established trends that link long ion-bound alkyl groups to higher melting points. The new ILs are also less viscous than a saturated standard (see bottom structure) at the same temperature. These features parallel those that underpin homeoviscous adaptation in certain organisms and are indirectly supportive of a fluid-mosaiclike nanoscale character.
- Murray, Samuel M.,O'Brien, Richard A.,Mattson, Kaila M.,Ceccarelli, Christopher,Sykora, Richard E.,West, Kevin N.,Davis Jr., James H.
-
body text
p. 2755 - 2758
(2010/07/06)
-