TY  - JOUR
A1  - Schmidt, Bernd
A1  - Kunz, Oliver
A1  - Petersen, Monib H.
T1  - Total syntheses of naturally occurring seimatopolide a and its enantiomer from chiral pool starting materials using a bidirectional strategy
JF  - The journal of organic chemistry
N2  - 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).
Y1  - 2012
U6  - https://doi.org/10.1021/jo302359h
SN  - 0022-3263
VL  - 77
IS  - 23
SP  - 10897
EP  - 10906
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Berger, René
A1  - Petersen, Monib H.
T1  - From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction
JF  - Synthesis
N2  - 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.
KW  - acetanilides
KW  - deacetylation
KW  - diazonium salts
KW  - palladium
KW  - Matsuda-Heck reaction
Y1  - 2013
U6  - https://doi.org/10.1055/s-0032-1316874
SN  - 0039-7881
VL  - 45
IS  - 9
SP  - 1174
EP  - 1180
PB  - Thieme
CY  - Stuttgart
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Petersen, Monib H.
A1  - Braun, Diana
T1  - 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
JF  - The journal of organic chemistry
N2  - (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.
Y1  - 2018
U6  - https://doi.org/10.1021/acs.joc.7b02944
SN  - 0022-3263
VL  - 83
IS  - 3
SP  - 1627
EP  - 1633
PB  - American Chemical Society
CY  - Washington
ER  -