57917-96-1Relevant academic research and scientific papers
A catalytic enantioselective route to hydroxy-substituted quaternary carbon centers: Resolution of tertiary aldols with a catalytic antibody
List, Benjamin,Shabat, Doron,Zhong, Guofu,Turner, James M.,Li, Anthony,Bui, Tommy,Anderson, James,Lerner, Richard A.,Barbas III, Carlos F.
, p. 7283 - 7291 (2007/10/03)
Aldolase antibody 38C2-catalyzed resolutions of tertiary aldols were studied. Tertiary aldols proved to be very good substrates for antibody catalyzed retro-aldol reactions. The catalytic proficiency, (k(cat)/K(M))/k(uncat), of the antibody for these reactions was on the order of 1010 M-1. A fluorogenic tertiary aldol allowed for the quantitative study of enantiomeric excess as a function of reaction conversion, revealing an E value of ca. 160 in this case. Study of a variety of substrates demonstrated that antibody-catalyzed retro-aldolization provides rapid entry to highly enantiomerically enriched tertiary aldols, typically > 95% ee, containing structurally varied, heteroatom-substituted quaternary carbon centers. The utility of this approach to natural product syntheses has been demonstrated with the syntheses of (+)-frontalin, the side chain of Saframycin H, and formal syntheses of (+)- and (-)-mevalonolactone.
SYNTHESIS OF THE PHEROMONES, (E)-3,7-DIMETHYL-2,7-OCTADIENYL PROPIONATE, (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL AND FRONTALIN FROM A COMMON INTERMEDIATE
Dhokte, U. P.,Rao, A. S.
, p. 811 - 822 (2007/10/02)
Ketal ester 9 has been prepared in five steps from methyl levulinate 4 (scheme 1).The propionate 1, diol 2 and (+/-) frontalin 3 were prepared from ester 9 employing the routes shown in scheme 2,3 and 4 respectively.The branched chain alkenes 13 and 20 were prepared conveniently from the primary alcohols 11 and 10 following the procedure of S.Wolff.Triethyl phosphonopropionate 7 has been prepared by methylating triethylphosphonoacetate with methyl iodide in the presence of sodium hydride.
CONVENIENT SYNTHETIC ROUTE TO (+/-) -FRONTALIN
Kongkathip, Boonsong,Sokkho, Rongsan,Kongkathip, Ngampong
, p. 1849 - 1850 (2007/10/02)
(+/-)-Frontalin was synthesized in a few steps sequence starting from ethyl acetoacetate involving intramolecular cyclization using palladium chloride as catalyst
