%0 Journal Article %1 ISI:000293497900020 %A Theurer, Matthias %A El Baz, Yana %A Koschorreck, Katja %A Urlacher, Vlada B. %A Rauhut, Guntram %A Baro, Angelika %A Laschat, Sabine %D 2011 %J European J. Org. Chem. %K chemie products,Polyketides,Total Biocatalysis,Computational chemistry,Natural from:alexanderdenzel rauhut synthesis theoretische stuttgart theochem %N 22 %P 4241–4249 %R 10.1002/ejoc.201100412 %T Chemoenzymatic synthesis of the C3-C11-fragment of borrelidin %U http://dx.doi.org/10.1002/ejoc.201100412 %X The ex-chiral pool synthesis of the Theodorakis C3-C11 fragment of borrelidin (I) by a chemoenzymic approach in nine steps and 12 \% overall yield starting from enantiopure methyl-branched preen gland wax esters is described. In the initial reaction, the wax ester II was (ω-1)-hydroxylated regioselectively by using a mutant of the cytochrome P 450 monooxygenase CYP102A1 as biocatalyst. The fourth stereocenter in the C3-C11 fragment III was generated by chiral auxiliary mediated alkylation. In order to explain the exptl. results of the alternative epimerization of an all-syn polypropionate, quantum chem. calcns. were performed at the B3LYP/cc-pVDZ level. ［on SciFinder(R)］ %@ 1099-0690

@article{ISI:000293497900020, abstract = {The ex-chiral pool synthesis of the Theodorakis C3-C11 fragment of borrelidin (I) by a chemoenzymic approach in nine steps and 12 {\%} overall yield starting from enantiopure methyl-branched preen gland wax esters is described. In the initial reaction, the wax ester II was (ω-1)-hydroxylated regioselectively by using a mutant of the cytochrome P 450 monooxygenase CYP102A1 as biocatalyst. The fourth stereocenter in the C3-C11 fragment III was generated by chiral auxiliary mediated alkylation. In order to explain the exptl. results of the alternative epimerization of an all-syn polypropionate, quantum chem. calcns. were performed at the B3LYP/cc-pVDZ level. ［on SciFinder(R)］}, added-at = {2019-02-15T17:47:57.000+0100}, author = {Theurer, Matthias and {El Baz}, Yana and Koschorreck, Katja and Urlacher, Vlada B. and Rauhut, Guntram and Baro, Angelika and Laschat, Sabine}, biburl = {https://puma.ub.uni-stuttgart.de/bibtex/2c0f013f62805aec60030f9553413dfa7/theochem}, doi = {10.1002/ejoc.201100412}, interhash = {42f2925da9d726760679f64c49eaa7ae}, intrahash = {c0f013f62805aec60030f9553413dfa7}, isbn = {1099-0690}, issn = {1434193X}, journal = {European J. Org. Chem.}, keywords = {chemie products,Polyketides,Total Biocatalysis,Computational chemistry,Natural from:alexanderdenzel rauhut synthesis theoretische stuttgart theochem}, month = aug, number = 22, pages = {4241–4249}, timestamp = {2019-02-15T16:47:57.000+0100}, title = {{Chemoenzymatic synthesis of the C3-C11-fragment of borrelidin}}, url = {http://dx.doi.org/10.1002/ejoc.201100412}, year = 2011 }