182952-48-3Relevant academic research and scientific papers
Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates
Hudlicky, Tomas,Endoma, Mary Ann A.,Butora, Gabor
, p. 2187 - 2192 (1996)
(5S,6R)-1-(2-Bromoethyl)-5,6-(propane-2,2-diyldioxy)cyclohexa-1,3-diene 6 is subjected to nucleophilic substitution reaction using C-, N-, O- and S-based nucleophiles. The yields of the products are compared with those obtained by direct microbial oxidation of the corresponding aromatic substrates. The enantiomeric excess and isolated yield for each compound are reported.
Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms
Endoma, Mary Ann,Bui, Vu P.,Hansen, Jeff,Hudlicky, Tomas
, p. 525 - 532 (2013/09/06)
The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.
Advanced intramolecular diels-alder study toward the synthesis of (-)- morphine: Structure correction of a previously reported Diels-Alder product
Butora, Gabor,Gum, Andrew G.,Hudlicky, Tomas,Abboud, Khalil A.
, p. 275 - 278 (2007/10/03)
A tricyclic ring system 18 containing all 5 chiral centers of the natural (-)-morphine skeleton has been synthesized in 9 steps. cis-Dienediol 11 was produced by a batch microbial dihydroxylation of (2-azidoethyl)benzene with the E. coli strain JM109(pDTG601). The key step in the synthesis was a thermal [4+2] intramolecular Diels-Alder cycloaddition of triene 16 which afforded the tricyclic adduct 17 in 62% yield. After deprotection, the absolute stereochemistry of the alcohol 18 was determined by X-ray crystallographic analysis. The previously reported Diels-Alder adduct 4a was deprotected and the absolute stereochemistry of the free alcohol was assigned by X-ray crystallography to have the structure 4c. This finding therefore constitutes the correction of the structure for 4a.
