Application of allylic substitutions in natural products synthesis
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| 024 | 7 | 0 | |a 10.1351/pac200476030495 |2 doi |
| 035 | |a (NATIONALLICENCE)gruyter-10.1351/pac200476030495 | ||
| 245 | 0 | 0 | |a Application of allylic substitutions in natural products synthesis |h [Elektronische Daten] |c [G. Helmchen, Martin Ernst, G. Paradies] |
| 520 | 3 | |a Synthesis routes are described, allowing all known jasmonoids as well as their enantiomers to be synthesized in enantiomerically and diastereomerically pure form. The routes are based on a set of closely related lactones containing an electrophilic allylic moiety, which are accessible via asymmetric Pd-catalyzed allylic alkylation. Regio- and diastereoselective SN2'-anti-reactions of the electrophilic lactones with organocopper compounds furnished 2,3-cis-disubstituted cyclopentenones, which were further transformed into the target compounds, i.e., 12-oxophytodienoic acid (12-OPDA) in excellent overall yields. The methodology also allowed iridoids and isoprostanes to be prepared. The configuration of an Archaea membrane lipid constituent containing cyclopentane rings was determined by total synthesis of a diol that was also obtained by degradation of the natural product. | |
| 540 | |a © 2013 Walter de Gruyter GmbH, Berlin/Boston | ||
| 700 | 1 | |a Helmchen |D G. |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | |
| 700 | 1 | |a Ernst |D Martin |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | |
| 700 | 1 | |a Paradies |D G. |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | |
| 773 | 0 | |t Pure and Applied Chemistry |d De Gruyter |g 76/3(2004-01-01), 495-505 |x 0033-4545 |q 76:3<495 |1 2004 |2 76 |o pac | |
| 856 | 4 | 0 | |u https://doi.org/10.1351/pac200476030495 |q text/html |z Onlinezugriff via DOI |
| 908 | |D 1 |a research article |2 jats | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1351/pac200476030495 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Helmchen |D G. |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ernst |D Martin |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Paradies |D G. |u Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Pure and Applied Chemistry |d De Gruyter |g 76/3(2004-01-01), 495-505 |x 0033-4545 |q 76:3<495 |1 2004 |2 76 |o pac | ||
| 900 | 7 | |b CC0 |u http://creativecommons.org/publicdomain/zero/1.0 |2 nationallicence | |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-gruyter | ||