Article
Chemistry, Organic
Bi Bali Judicael Tra, Abolle Abolle, Vincent Coeffard, Francois-Xavier Felpin
Summary: This paper presents a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The method allows for the selective synthesis of target products based on detailed knowledge of the reaction mechanisms, providing robust conditions for the preparation of natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
Lachlan Sharp-Bucknall, Tania, Jason L. Dutton
Summary: This article describes the synthesis and structural characterization of NO2-PhI(OTf)(2), a compound that is resistant to decomposition and has higher reactivity than previously misidentified PhI(OTf)(OAc), confirming the non-existence of PhI(OTf)(2) as an intermediate in oxidation reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Chunngai Hui, Andrey P. Antonchick
Summary: A concise synthesis of piperarborenine B is reported, which involves multiple steps including organocatalytic electrophilic amination and stereospecific oxidative ring contraction. The synthesis was achieved without the use of transition metals, directing groups or protecting groups, providing a novel strategy for the preparation of a non-symmetrical cyclobutane core.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
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
Yuan Jin, Kensuke Orihara, Fumiki Kawagishi, Tatsuya Toma, Tohru Fukuyama, Satoshi Yokoshima
Summary: The total synthesis of Haliclonin A was achieved through a series of reactions including Birch reduction/alkylation, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition, leading to the formation of the desired compound.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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)
Review
Chemistry, Multidisciplinary
Camille Rocq, Maxime Denis, Sylvain Canesi
Summary: Hypervalent iodine reagents are versatile and environmentally friendly compounds that have been widely used in multi-step syntheses for the formation of complex natural products. In this review, recent routes and strategies to produce complex natural products based on hypervalent iodines are described, emphasizing the advantages of these key reactants while acknowledging their limitations.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Organic
Duarte B. Clemente, Jaime A. S. Coelho
Summary: This review summarizes the synthetic strategies developed by several research groups in Portugal for the total synthesis of bioactive natural products, including alkaloids, cyclitols, fatty alcohols, phenylpropanoic acids, gamma-butyrolactones, xanthones, and nucleosides.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Michael P. Badart, Emma M. Barnes, Andrew P. Cording, Selena C. L. Gilmer, Ian D. Billinghurst, Veera V. Shivaji R. Edupuganti, Guillaume Lessene, Abigail R. Bland, Rebekah L. Bower, Zohaib Rana, Scott A. Ferguson, Helen K. Opel Reading, Gregory M. Cook, Rhonda J. Rosengren, Kurt L. Krause, Allan B. Gamble, John C. Ashton, Bill C. Hawkins
Summary: A second-generation enantiospecific synthesis of spiroleucettadine was described, with a focus on the anti-proliferative activity of synthetic samples compared to natural sources. Efforts to alter the structure at specific positions led to the synthesis of analogues showing similar anti-proliferative profiles against lung cancer cell lines.
Article
Chemistry, Applied
Maxime Denis, Samuel Blais, Sylvain Canesi
Summary: A stereoselective synthesis of isolycoricidine, a natural product belonging to the Amaryllidaceae alkaloids family, was achieved. The study also conducted a synthetic investigation on the main core of lycoricidine, resulting in the formation of analogues and a diastereomer of dihydrolycoricidine. The research utilized various strategies including oxidative phenol dearomatization, stereoselective Heck process, selective dihydroxylation, stereoselective reductions, and oxidative retro-Michael procedure as an amine-deprotecting group strategy. In addition, the study highlighted the usefulness of hypervalent iodines in total synthesis of natural products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Quanzheng Zhang, Zhao Yang, Qi Wang, Shuangwei Liu, Tao Zhou, Yankun Zhao, Min Zhang
Summary: In this study, the first asymmetric total synthesis of two hetidine-type C-20-diterpenoid alkaloids was reported. A highly regio- and diastereoselective 1,3-dipolar cycloaddition of an azomethine ylide was utilized to yield a chiral tetracyclic intermediate, serving as the basis for the asymmetric assembly of the hexacyclic hetidine skeleton. Another key transformation involved the dearomative cyclopropanation of the benzene ring and subsequent S(N)2-like ring opening to establish the B ring and install the equatorial C7-OH group.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Ye Zhang, Lei Zhang, Xiangbing Qi
Summary: This article provides a detailed examination of the intramolecular oxidative coupling between a ketone and a Weinreb amide for assembling the complex 1-azabicyclo[2.2.2]octane core structure of sarpagine alkaloids. Through precise late-stage manipulations of the ketone and Weinreb amide, divergent syntheses of (-)-trinervine, (+)-vellosimine, (+)-normacusine B, and (-)-alstomutinine C were achieved. Notable transformations in the synthesis include an aza-Achmatowicz/indole cyclization cascade, regioselective elimination reaction, and diastereoselective indole oxidative rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Minami Odagi, Kazuo Nagasawa
Summary: Alkaloids with fused polycyclic frameworks are attractive targets for synthesis due to their structural complexity and biological activities. This paper describes a strategy using oxidative phenolic coupling and regioselective intramolecular aza-Michael reaction to generate fused polycyclic frameworks, and its application in the total synthesis of (+)-gracilamine and various hasubanan alkaloids.
Article
Chemistry, Organic
Xiaohua Li, Qiuqin He, Renhua Fan
Summary: A process for synthesizing a variety of 4-amino indoles with N1 or C4 free amine groups has been reported. This process involves oxidative dearomatization, imine exchange, cascade 1,4-addition/cyclization/aromatization, and selective deprotection steps. The formed 4-amino indoles can be converted to 4,7-difunctionalized indoles via selective Friedel-Crafts alkylation.
ORGANIC CHEMISTRY FRONTIERS
(2022)