Article
Chemistry, Multidisciplinary
Brandon C. Derstine, Alina J. Cook, James D. Collings, Joseph Gair, Josep Sauri, Eugene E. Kwan, Noah Z. Burns
Summary: In this study, we report the first total synthesis and full stereochemical assignment of (+)-discorhabdin V. The synthesis was achieved through a highly convergent strategy enabled by scalable access to the two key components. Our work lays the foundation for future biological evaluation of nitrogen-bridged discorhabdins.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Atsushi Nakayama, Tenta Nakamura, Toshihiro Zaima, Saho Fujimoto, Sangita Karanjit, Kosuke Namba
Summary: The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jason An, Richard K. Jackson, Joseph P. Tuccinardi, John L. Wood
Summary: This paper presents an efficient, scalable, and concise approach for the synthesis of an advanced pyrroloiminoquinone synthetic intermediate (6b) using Larock indole synthesis. The synthetic utility of this intermediate is demonstrated by its ready conversion to makaluvamines A (1) and K (4).
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Immanuel Plangger, Tobias Pinkert, Klaus Wurst, Thomas Magauer
Summary: We have developed a concise asymmetric total synthesis method to access nine sesquiterpenoid alkaloids with four different tetra-/pentacyclic scaffolds in 5-8 steps. The key step of this synthesis is a bioinspired indole N-terminated cationic tricyclization, which enables the divergent synthesis of greenwayodendrines and polysin. By varying the precursor for the C2-substituted indole cyclization, the indole N- and C-termination can be switched, leading to the synthesis of greenwaylactams and polyveoline.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Katie A. A. Spence, Marie Hoffmann, Neil K. K. Garg
Summary: We report a concise approach to the synthesis of phenanthroindolizidine alkaloids, utilizing the interception of strained azacyclic alkynes in Pd-catalyzed reactions. Two types of strained intermediates, a functionalized piperidyne and a new strained intermediate, indolizidyne, were evaluated. These efforts resulted in the successful synthesis of three natural products: tylophorine, tylocrebine, and isotylocrebine, demonstrating the successful combination of strained azacyclic alkyne chemistry with transition-metal catalysis for the construction of complex heterocycles.
Article
Chemistry, Organic
Valerie Loesle, Olga Kataeva, Hans-Joachim Knoelker
Summary: The study presents the total synthesis of clausenalansine A, a recently discovered pyrano[3,2-a]carbazole alkaloid, through a synthetic strategy involving key steps such as Buchwald-Hartwig coupling and palladium(II)-catalyzed oxidative cyclization.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Xianhuang Zeng, Dale L. Boger
Summary: The total synthesis of (-)-strempeliopine involves a powerful SmI2-mediated and BF3 center dot OEt2-initiated dearomative transannular radical cyclization onto an indole, resulting in the formation of a quaternary center and the strategic C19-C2 bond in its core structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Ryohei Hanzawa, Haruhiko Fuwa
Summary: A collective asymmetric total synthesis of marine tricyclic alkaloids, cylindricines A-H, as well as the proposed structures of cylindricines I and J, was accomplished from a single common spirocyclic pyrrolidine intermediate in a concise manner. A tandem chemoselective oxidation/intramolecular aza-Michael addition/epimerization strategy was utilized to successfully construct the tricyclic skeleton. This work presents a versatile synthetic approach to the cylindricine family of marine tricyclic alkaloids.
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shuai Jiang, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji
Summary: A Co-catalyzed cyclization reaction of isocyanides, azides, and amines was developed to access quinazoline derivatives, featuring high atom economy, mild reaction conditions, excellent yields, and a broad substrate scope. The cascade reaction involved the formation of three to four C-N bonds and one or two rings, producing versatile intermediates for further transformations. The cobalt catalyst used in the reaction was found to be isolatable and reusable.
Article
Chemistry, Multidisciplinary
Franziska Spruner von Mertz, Ricardo Molenda, Sebastian Boldt, Alexander Villinger, Peter Ehlers, Peter Langer
Summary: A series of previously unknown 5,14-diphenylbenzo[j]naphtho[2,1,8-def][2,7]phenanthrolines, incorporating a 5-azatetracene and a 2-azapyrene subunit, were successfully synthesized using Pd-catalyzed cross-coupling reactions and a one-pot Povarov/cycloisomerization reaction. This synthetic approach enables extensive diversification of the heterocyclic core structure. The optical and electrochemical properties of these compounds were investigated through experimental and computational studies, revealing their closer electronic and optical resemblance to 2-azapyrenes rather than the typical characteristics of 5-azatetracene moieties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Quentin Dherbassy, Srimanta Manna, Chunling Shi, Watcharapon Prasitwatcharakorn, Giacomo E. M. Crisenza, Gregory J. P. Perry, David J. Procter
Summary: In this study, an enantioselective copper-catalyzed borylative cyclization was reported for the assembly of privileged pyrroloquinazolinone motifs. The reaction demonstrated high enantio- and diastereocontrol, yielding products with quaternary stereocenters. The utility of the products was further demonstrated through additional manipulations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yousuke Yamaoka, Takuro Yamakawa, Kaito Tateishi, Kiyosei Takasu
Summary: Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Suchen Zou, Zeyu Zhao, Hanmin Huang
Summary: In this study, a novel and efficient palladium-catalyzed reaction was developed for the regioselective and stereodivergent ring-closing of aminoenynes with aldehydes and boronic acids or hydrosilane. The reaction allows for the synthesis of a series of exocyclic 1,3-dienes bearing saturated N-heterocycles of 5- to 8-membered rings. It utilizes a simple Pd-catalyst and works under mild reaction conditions with a broad range of substrates. The resulting products serve as useful intermediates for chemical synthesis due to the versatility of the conjugated diene. Preliminary mechanistic details of the reaction are also uncovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
