TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
A1  - Schilde, Uwe
T1  - Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
JF  - European journal of organic chemistry
N2  - Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
KW  - Allylic compounds
KW  - Arenes
KW  - Oxygen heterocycles
KW  - Microwave chemistry
KW  - Rearrangement
KW  - Michael addition
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201501151
SN  - 1434-193X
SN  - 1099-0690
IS  - 34
SP  - 7602
EP  - 7611
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
T1  - Synthesis of Magnaldehydes B and E and Dictyobiphenyl B by Microwave-Promoted Cross-Coupling of Boronophenols
JF  - European journal of organic chemistry
N2  - Magnaldehydes B and E along with their 4'-methylated derivatives are naturally occurring 2,4'-biphenols that have been isolated from the Magnoliaceae. Herein, these natural products have been synthesized from a common intermediate, which was obtained by a microwave-promoted, hetero-geneously catalyzed, and protecting-group-free Suzuki-Miyaura coupling reaction in an aqueous medium. These reaction conditions were also successfully applied to a one-step synthesis of the slime mold metabolite dictyobiphenyl B.
KW  - Total synthesis
KW  - Natural products
KW  - Cross-coupling
KW  - Palladium
KW  - Biaryls
KW  - Phenols
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201500350
SN  - 1434-193X
SN  - 1099-0690
IS  - 17
SP  - 3760
EP  - 3766
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Schilde, Uwe
A1  - Kelling, Alexandra
T1  - Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions
JF  - The journal of organic chemistry
N2  - The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.
Y1  - 2015
U6  - https://doi.org/10.1021/acs.joc.5b00272
SN  - 0022-3263
VL  - 80
IS  - 9
SP  - 4223
EP  - 4234
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Riemer, Nastja
A1  - Hölter, Frank
T1  - Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionalization
JF  - European journal of organic chemistry
N2  - Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.
KW  - Arenes
KW  - Amides
KW  - C-C coupling
KW  - Cross-coupling
KW  - Palladium
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201500795
SN  - 1434-193X
SN  - 1099-0690
IS  - 26
SP  - 5826
EP  - 5841
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Paz, Cristian
A1  - Becerra, Jose
A1  - Silva, Mario
A1  - Burgos, Viviana
A1  - Heydenreich, Matthias
A1  - Schmidt, Bernd
A1  - Thu Tran, 
A1  - Vetter, Irina
T1  - (-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia tupa with Agonist Activity at Nicotinic Acetylcholine Receptor
JF  - Natural product communications : an international journal for communications and reviews
N2  - Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at alpha 3 beta 2/alpha 3 beta 4 nAChR and alpha 7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR
KW  - Lobelia tupa
KW  - Piperidine alkaloid
KW  - nAChR
KW  - Pentylsedinine
Y1  - 2015
SN  - 1934-578X
SN  - 1555-9475
VL  - 10
IS  - 8
SP  - 1355
EP  - 1357
PB  - NPC
CY  - Westerville
ER  - 
TY  - BOOK
A1  - Buddrus, Joachim
A1  - Schmidt, Bernd
T1  - Grundlagen der organischen Chemie
Y1  - 2015
SN  - 978-3-11-030559-3
PB  - de Gruyter
CY  - Berlin
ET  - 5., überarb. und aktualisierte Aufl.
ER  -