Article
Chemistry, Organic
Fangzhi Han, Guangju Liu, Xiuhe Zhao, Shunshun Du, Yahui Ding, Quan Zhang, Huiting Deng, Liang Wang, Yue Chen
Summary: In this study, the total synthesis of rakicidin F was successfully achieved, allowing the determination of its stereogenic centers. The macrolactonization reaction of rakicidin precursor was also investigated, with steric hindrance near C16-OH identified as a possible cause for the unsuccessful results.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Hongjun Jang, Soo Yeon Kwak, Dongjoo Lee, Juan Alegre-Requena, Hyoungsu Kim, Robert S. Paton, Deukjoon Kim
Summary: This study successfully achieved the introduction of halogens in the synthesis of (+)-srilankenyne through a sequence-sensitive process guided by conformational analysis and experimental studies.
Article
Chemistry, Organic
Fangzhi Han, Guangju Liu, Xuhai Zhang, Yahui Ding, Liang Wang, Yijing Wu, Yue Chen, Quan Zhang
Summary: For the first time, the 15-membered cyclic depsipeptide boholamide A and an epimer were prepared by total synthesis, leading to a revision of the C6 stereochemistry in the original proposed structure. The revised boholamide A was synthesized in 16 linear steps with an overall yield of 5.46%, facilitating investigations into its potential as a hypoxia-selective anticancer agent.
Article
Chemistry, Multidisciplinary
Akane Yamagishi, Yuki Egoshi, Makoto T. T. Fujiwara, Noriyuki Suzuki, Tohru Taniguchi, Ryuuichi D. D. Itoh, Yumiko Suzuki, Yoshiro Masuyama, Kenji Monde, Toyonobu Usuki
Summary: This study describes the total synthesis of foeniculoxin and demonstrates its phytotoxicity in plant cells. Foeniculoxin induces various defects in Arabidopsis thaliana leaf cells and causes aggregation of mitochondria around chloroplasts.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Liam J. Franov, Jacob D. Hart, Glenn A. Pullella, Christopher J. Sumby, Jonathan H. George
Summary: This article introduces the research content and importance of biomimetic synthesis, as well as the progress in the concise total synthesis and structural reassignment of hyperelodione D.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Peilin Tian, Wenkang Ye, Xiayan Zhang, Yi Tong, Pei-Yuan Qian, Rongbiao Tong
Summary: The increase in antibiotic resistance necessitates the development of new antibiotics with novel molecular structures and mechanisms of action. However, the discovery of new antibiotics and their progression into clinical use have been limited in recent decades. The potent anthracimycin antibiotic represents a significant advancement in this field, with its unique structural features and excellent biological activity against various bacteria, including drug-resistant strains. Researchers have successfully achieved the total synthesis of anthracimycin through a 10-step asymmetric synthesis, providing a reliable supply for further studies and allowing the preparation of analogues for structure-activity relationship studies.
Article
Chemistry, Multidisciplinary
David A. Evans, Jason J. Beiger, Jason D. Burch, Peter H. Fuller, Frank Glorius, Egmont Kattnig, David A. Thaisrivongs, William C. Trenkle, Joseph M. Young, Jing Zhang
Summary: The total syntheses of aflastatin A and its C3-C48 degradation fragment have been achieved, revealing a structural misassignment in the naturally derived degradation product. The revised absolute configurations of six stereogenic centers were also confirmed in this study.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Ramagonolla Kranthikumar
Summary: This study achieved a short and enantioselective synthesis of the 19-epi-BE-43547 A(2) chiral framework in a high yield. The synthetic strategy involved innovative methods such as Julia-Kocienski olefination and Z to E isomerization of olefin using a novel UV flow reactor. Additionally, unprecedented oxygen mediated hydroboration and the Krapcho decarboxylation of beta-keto lactone were observed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Sagar S. Thorat, Ravindar Kontham
Summary: This comprehensive review article focuses on showcasing the complete spectrum of efforts devoted towards the synthesis of diverse classes of furo-pyranones from the 1970s to 2020, emphasizing their importance in synthetic organic chemistry and medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xueying Wang, Yeelin Phang, Jiling Feng, Song Liu, Hong Zhang, Wenwei Fu, Hua Zhou, Gang Xu, Hongxi Xu, Changwu Zheng
Summary: The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. An efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.
Article
Chemistry, Organic
Jessica C. Neville, Michelle Y. Lau, Tilo Sohnel, Jonathan Sperry
Summary: Chitin-derived platforms have emerged as valuable chemical entities for nitrogenous fine chemicals construction independent of the Haber ammonia process. However, much of the research in this field has focused on achiral platforms, limiting the access to enantiopure, bio-based nitrogenous chemical space. In this study, dihydroxyethyl acetamidofuran (Di-HAF), a chiral synthon easily available from chitin, has been transformed into epi-leptosphaerin, a marine alkaloid. This work extends the concept of Haber-independent synthesis to enantiopure chemical space that is not routinely accessible from existing achiral platforms.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Plant Sciences
Andrea Areal, Marta Dominguez, Pim Vendrig, Susana Alvarez, Rosana Alvarez, Angel R. de Lera
Summary: The total synthesis and structural confirmation of homo- and heterodimeric bispyrrolidinoindoline dioxopiperazine alkaloids isolated from fungi and bacteria have been successfully achieved. The study revealed structural factors that determine the rate and efficiency of ring formation, leading to the formation of mixtures of diastereomers and their putative monomeric precursors, as well as an alternative pathway for dimer formation with a fused heterocycle.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Dattatraya H. Dethe, Appasaheb K. Nirpal
Summary: An efficient and convergent total synthesis of (+/-)-japonicol B and (-)-japonicol C has been achieved, utilizing Lewis acid-catalyzed Friedel-Crafts reaction for C-C and C-O bond formations, one pot Pd(OH)(2)/C-catalyzed isomerization/hydrogenation, and site selective sp(3) C-H oxidation as key steps in the synthetic route.
Article
Chemistry, Multidisciplinary
Wenqiang Zhou, Tao Zhou, Mengxing Tian, Yan Jiang, Jiaojiao Yang, Shuai Lei, Qi Wang, Chongzhou Zhang, Hanyue Qiu, Ling He, Zhen Wang, Jun Deng, Min Zhang
Summary: Through the development of a new method and key reactions, the concise, collective, and asymmetric total syntheses of four schizozygane alkaloids, including the first asymmetric synthesis, have been achieved in only 11-12 steps from tryptamines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Luke Hodson, Kevin J. Visagie, Michael-Phillip Smith, Leigh Loots, David Kuter, Tregen M. Snayer, Gareth E. Arnott
Summary: Inherently chiral calix[4]arenes with C-4-symmetry are rare and difficult to synthesise, but this study successfully obtained a high-yield product through a specific reaction. The use of a specific chiral group enabled the separation of the diastereomers formed, leading to the pure enantiomers.
CHEMICAL COMMUNICATIONS
(2021)
