Article
Chemistry, Organic
Xiaoyu Liu, Haidong Deng, Yingjun Jiang, Yang Cao, Zhe Wang, Xiaozhen Jiao, Ping Xie
Summary: (+/-) Commiphorane C, (+/-) commiphorane D, and their two isomers were successfully synthesized through a linear synthesis strategy. Biological evaluation revealed that some compounds could attenuate the overproduction of fibronectin, collagen I, and alpha-SMA, and exhibited low cytotoxicity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaoyu Liu, Haidong Deng, Yingjun Jiang, Yang Cao, Zhe Wang, Xiaozhen Jiao, Ping Xie
Summary: Commiphorane C, Commiphorane D, and their isomers were synthesized through a linear synthesis strategy in 14 steps. The biological evaluation showed that they can attenuate the overproduction of fibronectin, collagen I, and alpha-SMA in rat renal proximal tubular cells induced by TGF-beta 1.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shengkun Hu, Yefeng Tang
Summary: This paper reports the enantioselective total synthesis of dysiherbols A, C, and D using a photo-induced quinone-alkene [2 + 2] cycloaddition and a tandem [1,2]-anionic rearrangement/cyclopropane fragmentation as key elements. The originally proposed structures of dysiherbols C and D were revised based on the synthesis. Computational studies revealed insights into the unprecedented [1,2]-anionic rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Suhas Ravindra Bavikar, Hong-Jay Lo, Chebolu Naga Sesha Sai Pavan Kumar, Rong-Jie Chein
Summary: Herein, an enantioselective total synthesis of (-)-panduratin D, a novel secondary metabolite against human pancreatic cancer cells, is reported. The synthesis was completed in nine steps and involved various key features including Sonogashira coupling, anionic Snieckus-Fries rearrangement, directed ortho metalation, tandem Si -> C alkyl rearrangement/Claisen-Schmidt condensation, and chiral boron complex-promoted asymmetric Diels-Alder cycloaddition.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Lukas Fritz, Sebastian Wienhold, Sabrina Hackl, Thorsten Bach
Summary: The synthesis of pulvomycin D was achieved through a new strategy involving aldol reaction, esterification, and Heck reaction. Removal of protective groups and olefin formation were crucial steps in completing the synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Jia-Tian Lu, Yingxiao Zong, Xiaodong Yue, Junke Wang
Summary: The enantioselective synthesis of (+)-isolysergol was achieved in 18 steps with an overall yield of 11% from (2R)-(+)-phenyloxirane. Key steps included a stereoselective intramolecular 1,3-dipolar addition of nitrone with terminal olefin and a Cope elimination to form the D ring. A rhodium-catalyzed intramolecular [3 + 2] annulation of a benzene ring with alpha-imino carbenoid was designed for the late-stage synthesis of the 3,4-fused indole scaffold.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tomas Vieira de Castro, David M. M. Huang, Christopher J. J. Sumby, Andrew L. L. Lawrence, Jonathan H. H. George
Summary: A concise method for the synthesis of a stereochemically complex compound, peshawaraquinone, from an achiral precursor, dehydro-alpha-lapachone, via unsymmetrical dimerization is reported. The formation of the compound involves reversible oxa-6 pi-electrocyclizations and base-catalyzed dimerization, resulting in the formation of six stereocenters through an intramolecular (3 + 2) cycloaddition. Combining the generation and in situ dimerization of dehydro-alpha-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.
Article
Chemistry, Organic
Yassin M. Elbatrawi, Taylor Gerrein, Avraz Anwar, Kamlesh M. Makwana, David Degen, Richard H. Ebright, Juan R. Del Valle
Summary: We have achieved the total synthesis and configurational assignment of pargamicin A, a highly oxidized nonribosomal peptide that effectively inhibits the growth of drug-resistant bacteria. Our synthetic strategy involves late-stage piperazine ring formation and careful selection of condensation reagents to assemble the densely substituted hexapeptide backbone. This work facilitates the synthesis of pargamicin derivatives for structure-activity relationship studies and provides insights into accessing other piperazic acid-containing natural products with steric congestion.
Article
Chemistry, Organic
Yinxin Liu, Jun Liu, Chuanfang Zhao, Yuguo Du
Summary: The stereoselective total synthesis of siladenoserinols A and D was achieved using carbohydrates as a chiral template. The key feature of this work is the construction of the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction, which could facilitate bioactivity investigation of siladenoserinols.
Article
Chemistry, Multidisciplinary
Xin Shu, Chong-Chong Chen, Tao Yu, Jiayi Yang, Xiangdong Hu
Summary: Spiroxins A, C, and D are metabolites identified in the marine fungal strain LL-37H248, with unique polycyclic structures and intriguing biological activities. Researchers achieved the enantioselective total synthesis of (-)-spiroxins A and C, as well as the first total synthesis of (-)-spiroxin D, through a series of reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Maximilian Haider, Goh Sennari, Alina Eggert, Richmond Sarpong
Summary: This research presents a concise synthesis method for cephanolides A-D of Cephalotaxus norditerpenoids, utilizing a common late-stage synthetic intermediate and employing chemical network analysis and Csp(2)-Csp(3) cross-coupling for efficient construction of the carbon framework. Strategic late-stage oxidations were crucial in accessing all congeners of the benzenoid cephanolides isolated to date.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
William P. Thomas, Sergey Pronin
Summary: Paxilline-type indoloterpenoids, a large family of secondary metabolites, exhibit unique molecular architectures and a diverse set of biological activities, including neurological and insecticidal activities, modulation of lipid balance, and inhibition of mitosis. Organic chemists have been fascinated by the uniting polycyclic motif and the diversity of individual structural features of paxilline indoloterpenoids for the past four decades, leading to the development of numerous syntheses. The increasing diversity of structural motifs made accessible by application of this chemistry has led to the exploration of new synthetic methods and artificial assembly of terpenoid natural products from different families.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Plant Sciences
Takumi Abe, Ren Nakajima, Toshiki Yamashiro, Daisuke Sawada
Summary: In this study, Echinosulfonic acid D, a sponge metabolite with recently reassigned structure, was synthesized for the first time. The key step involved the double indolization of dimethylbarbituric acid using the umpolung indole reagent, followed by a hydrolysis/ decarboxylation/esterification sequence.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Plant Sciences
Masahito Yoshida, Tomoya Matsushita, Shinji Kondo, Hiroko Isoda, Hideo Kigoshi
Summary: The structure of trichomide D has been revised through total synthesis, and the configuration of the chlorohydrin moiety was found to be a pivotal factor for exhibiting potent cytotoxicity against cancer cells.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Zhongliu Sun, Xin Fan, Zezhong Sun, Zhijie Li, Lihua Niu, Hao Guo, Zhiqiang Ren, Yunxia Wang, Xiangdong Hu
Summary: This article reports a diverse strategy for the total synthesis of (-)-Ceforalide B and (-)-cephanolides B-D through an olefination/67r-electrocyclization/oxidative aromatization cascade and benzylic aerobic oxidations enabled by the Co(OAc)2middot4H2O/ bromide salt/O2/PPh3/N-hydroxyphthalimide system.
