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, Multidisciplinary
Jia-Xuan Liu, Shi-Peng Zhang, Feng-Sen Sun, Hui Li, Ya-Ling Gong, Shi-Chao Lu, Shu Xu
Summary: In this study, Naphthospironone A, a polyhydroxy cagelike bioactive natural product, was synthesized for the first time. The spiro[bicyclo[3.2.1]octane-pyran] core was constructed by an acid-promoted epoxide-opening lactonisation and a base-induced intramolecular aldol-type cyclisation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Julian Baars, Isabelle Grimm, Dirk Blunk, Joerg-Martin Neudoerfl, Hans-Guenther Schmalz
Summary: A 12-step total synthesis of the natural product dysiherbol A was achieved, revealing the need for revision of the originally proposed structure and absolute configuration. The synthesis involved key steps including Cu-catalyzed addition/enolate-trapping, Au-catalyzed double cyclization, and late installation of the C5-bridgehead methyl group. Spectroscopic measurements confirmed the identity of the synthetic compound with the natural product but with an opposite molecular rotation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yi-Peng Zhang, Shufei Du, Ying Ma, Weixin Zhan, Wen Chen, Xiaodong Yang, Hongbin Zhang
Summary: In this study, we present a structure-unit-based asymmetric total synthesis of sinulochmodin C, a norcembranoid diterpenoid with a unique structure. Our synthetic route involves several key reactions, including intramolecular double Michael addition, vinylogous hydroxylation/oxidation, transannular oxa-Michael addition, and bioinspired transformation. The successful total synthesis of sinulochmodin C demonstrates the effectiveness of our approach.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Junli Ao, Chao Sun, Bolin Chen, Na Yu, Guangxin Liang
Summary: Total syntheses of two Isodon diterpenes, isorosthin L and isoadenolin I, are achieved through a diastereoselective intermolecular aldol reaction and a subsequent radical cyclization. The study provides a synthetic strategy for the efficient construction of a complex intermediate and is of great significance for the synthesis of Isodon diterpenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Debobrata Paul, Ashis Kundu, Sanu Saha, Rajib Kumar Goswami
Summary: This feature article highlights total synthesis as a reliable tool for confirming the structure of natural products. Despite advances in spectroscopic techniques, structural misassignments of natural products remain common. Recent case studies have shown that chemical synthesis can be used to revise the structures of natural products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yuuki Watanabe, Hisahiro Morozumi, Hiroyuki Mutoh, Koichi Hagiwara, Masayuki Inoue
Summary: The paper presents a total synthesis of batrachotoxin based on a convergent strategy, involving a 22-step sequence. Enantiopure fragments were prepared and connected through a C(sp(2))-C(sp(2)) coupling reaction. The synthesis was completed through a series of optimized functionalizations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yuuki Watanabe, Hisahiro Morozumi, Hiroyuki Mutoh, Koichi Hagiwara, Masayuki Inoue
Summary: In this study, a total synthesis of batrachotoxin was achieved using a newly devised convergent strategy. The researchers successfully prepared enantiopure fragments of the AB-ring and D-ring, and connected them through a crucial C(sp(2))-C(sp(2)) coupling reaction. By optimizing the functionalizations, the team realized the formation of oxazepane, carbon chain extension, and pyrrole carboxylic acid condensation to deliver batrachotoxin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jackson A. Gartman, Uttam K. Tambar
Summary: The scientific community has shown great interest in anthraquinone-based compounds due to their therapeutic properties and challenging structural elements. In recent decades, various architecturally beautiful natural products have been synthesized using two main strategies, either through early-stage synthesis of anthraquinone and further system elongation, or late-stage introduction of the anthraquinone ring moiety. This article describes selected syntheses of complex anthraquinone monomers and dimers from the past 20 years, with a focus on the retrosynthetic disconnections that shape the anthraquinone-installation strategy.
Article
Chemistry, Multidisciplinary
Xikang Zheng, Yan Li, Mengtie Guan, Lingyue Wang, Shilong Wei, Yi-Cheng Li, Chin-Yuan Chang, Zhengren Xu
Summary: A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include one-pot two-enzyme-catalyzed oxidative dimerization and regioselective bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Mizushi Yanagihara, Kanae Nakahara, Naoki Kishimoto, Towa Abe, Satoshi Miura, Shogo Misumi, Makoto Sako, Mitsuhiro Arisawa, Kenichi Murai
Summary: The first total synthesis of marine sesterterpenoid ansellone G (2) has been accomplished. The hydrobenzopyran skeleton of ansellone G (2) was synthesized through the Prins cyclization reaction of a chloro-substituted homoallyl alcohol. The HIV latency-reversing activity of the synthesized compounds was also evaluated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Mizushi Yanagihara, Kanae Nakahara, Naoki Kishimoto, Towa Abe, Satoshi Miura, Shogo Misumi, Makoto Sako, Mitsuhiro Arisawa, Kenichi Murai
Summary: The first total synthesis of marine sesterterpenoid ansellone G and phorbadione was achieved, and their HIV latency-reversing activity was evaluated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Tomoya Mashiko, Yuta Shingai, Jun Sakai, Shogo Kamo, Shinya Adachi, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this study, the first total synthesis of cochlearol B, a meroterpenoid natural product with a unique pentacyclic structure, was described. Key steps including oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition allowed efficient access to cochlearol B with a longest linear sequence of 16 steps and 9% overall yield. Single-crystal X-ray crystallographic analysis confirmed the stereochemistry of cochlearol B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Debobrata Paul, Subhendu Das, Sanu Saha, Himangshu Sharma, Rajib Kumar Goswami
Summary: The intramolecular Heck reaction plays a significant role in synthesizing natural products by constructing various cyclic scaffolds. It serves as a strategic step in the synthesis of different natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
