78651-85-1Relevant academic research and scientific papers
Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: Synthesis of Sansalvamide A
Morales-Serna, Jose Antonio,Sanchez, Ericka,Velazquez, Ricardo,Bernal, Jorge,Garcia-Rios, Erendira,Gavino, Ruben,Negron-Silva, Guillermo,Cardenas, Jorge
experimental part, p. 4940 - 4948 (2010/11/24)
A facile and mild macrolactonization reaction of ω-hydroxy acids was developed based on the transesterification of benzotriazole esters. Treatment of ω-hydroxy acids with 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) and 1-hydroxy benzotriazole (HOBT) in chloroform provided macrolactones in excellent yields. The reactions were performed under basic, neutral and acidic conditions using N,N-dimethylaminopyridine (DMAP), tetrabutylammonium tetrafluoroborate (TBABF4) and BF3·Et2O, respectively. A calcined hydrotalcite was also used instead of DMAP. Finally, to test the scope of the protocol in the synthesis of biologically relevant macrolactones, the total synthesis of Sansalvamide A was carried out.
Synthesis of 14-hydroxytetra- and 15-hydroxypentadecanoic acids
Zakharkin, L. I.,Guseva V. V.,Pryanishnikov A. P.
, p. 658 - 661 (2007/10/02)
14-Hydroxytetradecanoic and 15-hydroxypentadecanoic acids were synthesized from 1,10-decanedicarboxylic and 1,11-undecanedicarboxylic acids.The diesters of the latter were reduced to the diols, from which the chlorohydrins were obtained by reaction with hydrogen chloride.The use of these chlorohydrins in the sodiomalonic synthesis leads to the hydroxy carboxylic acids.
