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S. Kalidindi, W. B. Jeong, A. Schall, R. Bandichhor, B. Nosse, O. Reiser, Angew. Chem. 2007, 119, 6478-6481; Angew. Chem. Int. Ed. 2007, 46, 6361-6363
Web edition: http://dx.doi.org/10.1002/anie.200701584
The first enantioselective synthesis of Arglabin and its dimethylamino adduct, showing promising results in the treatment of various tumors, has been achieved.
R. Patil,
S. Elz,
O. Reiser, Bioorg. Med. Chem. Lett. 2006, 16, 672-676
Web edition: http://dx.doi.org/10.1016/j.bmcl.2005.10.030
New analogues of histaprodifen with polar side chains have been stereoselectively synthesized and evaluated as histamine H1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H1-receptor agonism (relative potency 12%).
R. Weisser,
W. Yue,
O. Reiser, Org. Lett. 2005, 7, 5353-5356
Web edition: http://dx.doi.org/10.1021/ol051457m
A short and enantioselective synthesis of cis-fused 5-oxo-furo[2,3-b]furans, being found in many spongiane diterpenoid natural products, is reported starting from inexpensive methyl 2-furoate. Moreover, the acid-catalyzed rearrangement of the furo[2,3-b]furan framework A to B is observed for some derivatives, suggesting a simple connection between natural products differing in the absolute configuration of the 3a,6a ring junction.
G. Heimgärtner, D. Raatz, O. Reiser, Tetrahedron 2005, 61, 643-655
Web edition: http://dx.doi.org/10.1016/j.tet.2004.10.086
A highly efficient synthesis of swainsonine and 2,8a-di-epi-swainsonine was developed starting from readily available pyridine and 3-hydroxypyridine. In particular, it was demonstrated that the mixture of simple indolizidines, i.e. lentignosine and epi-lentiginosine, being readily available by a number of different synthetic routes, can be directly converted to swainsonine.
B. Nosse, R. B. Chhor, W. B. Jeong, C. Böhm, O. Reiser, Org. Lett. 2003, 5, 941-944
Web edition: http://dx.doi.org/10.1021/ol034141s
Bicyclic and tricyclic -butyrolactones with 5,7-, 5,6,5-, 5,6,6-, or 5,7,5-fused ring systems, being found in xanthanolides, eudesmanolides, and guaianolides, were readily synthesized from methyl furan-2-carboxylic acid. Key steps were a copper(I)-catalyzed asymmetric cyclopropanation, Sakurai allylations, intramolecular ene reactions, and ring-closing metathesis reactions.
R.B. Chhor, B. Nosse, S. Sörgel, C. Böhm, M. Seitz, O. Reiser, Chem. Eur. J. 2003, 9, 260-270
Web edition: http://dx.doi.org/10.1002/chem.200390019
The development of a new method for the enantioselective synthesis of disubstituted -butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)-protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I)-catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.
Peter Kreitmeier - 04.07.2011 07:33
