Article
Chemistry, Multidisciplinary
Kaixiang Xu, Shan Mu, Huijuanzi Rao, Jialei Hu, Hanfeng Ding
Summary: The asymmetric total syntheses of (+)-vulgarisins A-E, which share a rare and highly oxygenated [5-6-4-5] tetracyclic core structure that were isolated from P. vulgaris Linn., have been described for the first time in a divergent manner. Key transformations include: 1) a catalytic asymmetric intramolecular cyclopropanation to forge the A ring bearing desired stereochemistry at C14; 2) a one-pot borylation/conjugate addition process for creation of the C1-C11 bond; 3) a Wolff ring contraction to assemble the bicyclo[3.2.0]heptane subunit (CD rings); and 4) a stereocontrolled pinacol cyclization for construction of the central B ring of the natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Plant Sciences
Tian Tian, Minghan Li, Wei Feng, Yalong Ding, Zhaoyu Li, Zheng Shi, Tong Shen
Summary: The first total synthesis of coryaurone A was achieved with an efficient route and a high overall yield. A series of analogues were also synthesized with good yields, and their cytotoxic activities were evaluated.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Ji Soo Shin, Jaeyeon Lee, Sunkyu Han, Hee-Yoon Lee
Summary: Gold-catalyzed bicycloketalization of alkyne-diols provides synthetic advantages and allows for orthogonal protecting group manipulation of multiple hydroxyl groups. A newly developed divergent synthetic route to attenols A and B successfully overcomes the issue of isomerization between these two natural products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Koichiro Ota, Taiki Watanabe, Shuntaro Igarashi, Shinnosuke Okazaki, Kazuo Kamaike, Hiroaki Miyaoka
Summary: This study reports the stereoselective total syntheses of the enantiomers of the unique 3/10 bicyclic skeletal sesquiterpenoids, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition, intramolecular S(N)2 reaction, and pi-facial selective dihydroxylation.
Article
Chemistry, Multidisciplinary
Jiawei Sun, Yuan Chen, Sherif Shaban Ragab, Wei Gu, Ziqiang Tang, Yuexun Tang, Wenjun Tang
Summary: In this study, an unsaturation-functionalization strategy was applied to address the C19-hydroxylation issue for efficient synthesis of polyhydroxylated steroids. The synthetic method featured an effective asymmetric dearomative cyclization and various reactions to introduce the polyhydroxy functionalities. Ultimately, the total synthesis of 19-hydroxysarmentogenin and ouabagenin was achieved, demonstrating the synthetic versatility and practicality of these polyhydroxylated steroids in the search for new therapeutic agents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lei Li, Hua-Fei Yang, Qian-Hui Ding, Kun Wei, Yu-Rong Yang
Summary: We report the first utilization of the metallaphotoredox-enabled deoxygenative arylation of alcohols in natural product total synthesis. The coupling of 4-bromo-quinoline or 4-bromo-6-methoxyquinoline with quincorine or quincoridine was successfully achieved using this method. The synthesis of cinchona alkaloids was efficiently prepared.
Article
Biochemistry & Molecular Biology
Jing Chen, Yangyang Jiang, Jialei Yan, Chao Xu, Tao Ye
Summary: The first total syntheses of cyclic depsipeptides colletopeptide A and colletotrichamide A have been achieved through a series of transformations. By constructing a cyclic tridepsipeptide derivative as a key intermediate, followed by late-stage incorporation of the mannose fragment, the synthesis of colletotrichamide A and desilylation of the common intermediate led to the confirmation of the absolute stereochemistry of the natural products.
Article
Chemistry, Multidisciplinary
Gleb A. Chesnokov, Karl Gademann
Summary: Terpenoids are a class of natural compounds with diverse structures and bioactivities, which has attracted significant interest from the chemical community in the past 150 years. The presence of strained small rings in terpenoids makes their chemical synthesis challenging due to limited methods and stability issues. This feature article discusses recent examples of total syntheses of terpenoids with complex carbon frameworks featuring small rings, with a focus on the new developments in strategic and tactical approaches to constructing such systems.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yan Zong, Ze-Jun Xu, Rong-Xiu Zhu, Ai-Hong Su, Xu-Yuan Liu, Ming-Zhu Zhu, Jing-Jing Han, Jiao-Zhen Zhang, Yu-Liang Xu, Hong-Xiang Lou
Summary: An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is described in this study. The bioinspired and divergent synthesis involves an oxidative 1,3-dicarbonyl radical-initiated cyclization and cyclodehydration of a common precursor to forge the central ring of the manginoids and guignardones. Key synthetic steps include silica-gel-promoted semipinacol rearrangement and the Suzuki-Miyaura reaction of vinyl bromide for fragment coupling, enabling the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Akira Hirose, Ayumu Watanabe, Kohei Ogino, Masanori Nagatomo, Masayuki Inoue
Summary: Rhamnofolane, tigliane, and daphnane diterpenoids are structurally complex natural products with multiple oxygen functionalities, and a new synthetic strategy was developed for the total syntheses of five representative members of these families. This unified synthetic route required only 16-20 total steps, demonstrating exceptional efficiency.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Haiyong Yu, Junhao Zhang, Dongxu Ma, Xiaotong Li, Tao Xu
Summary: This article reports the first enantioselective total synthesis of (-)-caulamidine D and (-)-isocaulamidine D. Their absolute configurations were determined through X-ray crystallography. It was also found that the isolated natural samples exist as TFA salts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Biochemistry & Molecular Biology
Bichu Cheng, Lili Song, Fener Chen
Summary: Huperzine alkaloids, particularly Huperzine A, have shown potent inhibitory activity against acetylcholine esterase. The synthesis of Huperzine A has led to significant progress in the field and has also contributed to the total synthesis of other Huperzine alkaloids. This review focuses on the synthetic organic chemistry of Huperzines, as well as briefly covering their biosynthesis and medicinal chemistry.
NATURAL PRODUCT REPORTS
(2023)
Article
Multidisciplinary Sciences
K. C. Nicolaou, Saiyong Pan, Yogesh Shelke, Stephan Rigol, Ruiyang Bao, Dipendu Das, Qiuji Ye
Summary: A unified synthetic route for the total syntheses of eribulin and a macrolactam analog of halichondrin B has been successfully developed. The synthetic strategy involves the use of a reverse approach to construct cyclic ether structural motifs and a modified intramolecular cyclization reaction to establish the carbon macrocyclic framework of eribulin. These syntheses validate the effectiveness of the reverse approach in constructing cyclic ether structural motifs and provide inspiration and opportunities in the field of halichondrin and related polycyclic ether compounds.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2022)
Article
Chemistry, Organic
Yi Cui, Jun Ren, Jiayuan Lv, Zhongwen Wang
Summary: An efficient synthesis of the aza-[5.7.6.5] tetracyclic core structure of calyciphylline D-type Daphniphyllum alkaloids has been achieved, featuring diastereoselective cyclopropanation and a [3 + 2] IMCC strategy, as well as gram-scale preparation in each step.
Article
Chemistry, Multidisciplinary
Mansour D. Kerim, Laurent Evanno, Laurent Ferrie
Summary: This study describes the first total syntheses of representative congeners of the Mycaperoxides family using a stereodivergent approach. The researchers successfully synthesized several Mycaperoxides and established a pertinent database for further studies, confirming their original assignment.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Dylan Dagoneau, Zhengren Xu, Qian Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Antonin Clemenceau, Qian Wang, Jieping Zhu
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Multidisciplinary
Thomas Buyck, Delphine Pasche, Qian Wang, Jieping Zhu
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Multidisciplinary
Cyril Piemontesi, Qian Wang, Jieping Zhu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Organic
Guanyinsheng Qiu, Qian Wang, Jieping Zhu
Article
Chemistry, Organic
Martina Spallarossa, Qian Wang, Renata Riva, Jieping Zhu
Article
Chemistry, Multidisciplinary
Shuo Tong, Aurore Limouni, Qian Wang, Mei-Xiang Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Hua Wu, Qian Wang, Jieping Zhu
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Mathias Mamboury, Qian Wang, Jieping Zhu
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Xu Bao, Qian Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Shuo Tong, Cyril Piemontesi, Qian Wang, Mei-Xiang Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Shuo Tong, Shun Zhao, Qing He, Qian Wang, Mei-Xiang Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Yang Wang, Qian Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Wangqing Kong, Qian Wang, Jieping Zhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Review
Chemistry, Multidisciplinary
Mariateresa Giustiniano, Andrea Basso, Valentina Mercalli, Alberto Massarotti, Ettore Novellino, Gian Cesare Tron, Jieping Zhu
CHEMICAL SOCIETY REVIEWS
(2017)
