@article{SchmidtKunzPetersen2012,
  author    = {Schmidt, Bernd and Kunz, Oliver and Petersen, Monib H.},
  title     = {Total syntheses of naturally occurring seimatopolide a and its enantiomer from chiral pool starting materials using a bidirectional strategy},
  series = {The journal of organic chemistry},
  volume    = {77},
  journal   = {The journal of organic chemistry},
  number    = {23},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/jo302359h},
  pages     = {10897 -- 10906},
  year      = {2012},
  abstract  = {Enantioselective total syntheses of both enantiomers of the recently isolated decanolide natural product seimatopolide A are described. The C-2-symmetric building blocks (R,R)-hexa-1,5-diene-3,4-diol (derived from D-mannitol) and its enantiomer (derived from L-(+)-tartrate) serve as key starting materials, which are elaborated in a bidirectional way using a selective mono-cross-metathesis, regio- and stereoselective epoxidation, and regioselective reductive epoxide opening to furnish the first fragment. Both enantiomers of the second fragment, 3-hydroxypent-4-enoic acid, were conveniently obtained through a lipase-catalyzed kinetic resolution and merged with the first fragment via Shiina esterification. An E-selective ring-closing metathesis was used to access the 10-membered lactone. A comparison of the specific optical rotations of synthetic seimatopolides with those reported for the natural product suggests that the originally assigned (3R,6R,7R,9S)-configuration should be corrected to (3S,6S,7S,9R).},
  language  = {en}
}
@article{SchmidtElizarovBergeretal.2013,
  author    = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and Petersen, Monib H.},
  title     = {From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction},
  series = {Synthesis},
  volume    = {45},
  journal   = {Synthesis},
  number    = {9},
  publisher = {Thieme},
  address   = {Stuttgart},
  issn      = {0039-7881},
  doi       = {10.1055/s-0032-1316874},
  pages     = {1174 -- 1180},
  year      = {2013},
  abstract  = {A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization.},
  language  = {en}
}
@article{SchmidtPetersenBraun2018,
  author    = {Schmidt, Bernd and Petersen, Monib H. and Braun, Diana},
  title     = {Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C-2-Symmetric Building Block Using Olefin Metathesis Reactions},
  series = {The journal of organic chemistry},
  volume    = {83},
  journal   = {The journal of organic chemistry},
  number    = {3},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.7b02944},
  pages     = {1627 -- 1633},
  year      = {2018},
  abstract  = {(5R,6S)-6-Acetoxy-5-hexadecanolide (MOP) is the oviposition pheromone of the mosquito Cx. quinquefasciatus, a vector of pathogens causing a variety of tropical diseases. We describe and evaluate herein three syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C-2-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in situ conversion of a Ru-carbene to a Ru-hydride.},
  language  = {en}
}