Aza-Annulation Strategies in Alkaloid Total Synthesis

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Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Qian Wang, Jieping Zhu, Anne-Clémence Corminboeuf, Takuji Fujii, Simone Gallarati

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

Streamlined Alkylation via Nickel-Hydride-Catalyzed Hydrocarbonation of Alkenes

Xile Hu, Chao Fan, Srikrishna Bera, Zhikun Zhang

Compounds rich in sp(3)-hybridized carbons are desirable in drug discovery. Nickel-catalyzed hydrocarbonation of alkenes is a potentially efficient method to synthesize these compounds. By using abundant, readily available, and stable alkenes as pro-nucleo ...

2022

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

Qian Wang, Jieping Zhu, Bastien Delayre

The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new s ...

2021

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Xile Hu, Srikrishna Bera, Deyun Qian

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation metho ...

AMER CHEMICAL SOC2021

Enantioselective Total Synthesis of (+)-Alstilobanine C, (+)-Undulifoline, and (-)-Alpneumine H

Qian Wang, Jieping Zhu, Cyril Piemontesi, Guang Li, Nicolas David Gaeng

We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

Wiley-VCH Verlag GmbH2021

Diamine Synthesis via the Nitrogen-Directed Azidation of sigma- and pi-C-C Bonds

Jérôme Waser, Mingming Wang

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. ...

2021

Method and system for producing a carbonate-containing species-rich, nitrogen-containing species-free solution

Lyesse Laloui, Dimitrios Terzis

A method for producing a carbonate-containing species-rich, nitrogen-containing species-free solution from a urea-rich solution is proposed. The method comprising the steps of: providing a first reservoir comprising a first mixture including urea and a cat ...

2021

Heat stress reduces the contribution of diazotrophs to coral holobiont nitrogen cycling

Anders Meibom, Nils Rädecker, Claudia Isabella Pogoreutz, Gabriela Hannah Holligan Perna

Efficient nutrient cycling in the coral-algal symbiosis requires constant but limited nitrogen availability. Coral-associated diazotrophs, i.e., prokaryotes capable of fixing dinitrogen, may thus support productivity in a stable coral-algal symbiosis but c ...

2022

Engaging 1-Alkynyl Triazenes in Transition Metal-Catalyzed and Fluorinative Transformations

Jin Fay Tan

Triazenes have garnered great attention for their anti-cancer properties and versatility in organic chemistry. Recently, a novel synthesis of 1-alkynyl triazenes was reported. This thesis describes the compatibility, reactivity and applications of 1-alkyny ...

EPFL2021

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Qian Wang, Jieping Zhu, Dylan Jean Robert Dagoneau

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

WILEY-V C H VERLAG GMBH2020

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Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Qian Wang, Jieping Zhu, Dylan Jean Robert Dagoneau

WILEY-V C H VERLAG GMBH2020

Heat stress reduces the contribution of diazotrophs to coral holobiont nitrogen cycling

Anders Meibom, Nils Rädecker, Claudia Isabella Pogoreutz, Gabriela Hannah Holligan Perna

2022