Article
Chemistry, Organic
Yang Liu, Ziyang Zhao, Chao Hu, Chuanfang Zhao, Jun Liu, Yuguo Du
Summary: An efficient stereoselective synthesis of brevipolide M was achieved in 13 linear steps with an overall yield of 17.8% based on a chiron approach. The key steps involved a tandem Wittig olefination-tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM)-double-bond migration in one-pot processes.
Article
Chemistry, Multidisciplinary
Lu Chen, Kejing Xie, Jingyang Zhang, Liansuo Zu
Summary: This paper reports a direct spirocyclization approach for the chemical synthesis of spiro[cyclohexane-2-indoline] alkaloids. The absolute stereochemistry was introduced by a desymmetrizing Dieckmann condensation, and the relative stereochemistry was controlled by manipulating the kinetic and thermodynamic pathways of the spirocyclization. It is demonstrated that a common lactone-type intermediate, rather than the proposed diester-type alkaloid precursor, can bridge the chemical synthesis of this class of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kapil Sharma, Naresh Surineni, Sayani Das, Shivajirao L. Gholap
Summary: A concise and divergent chiron approach starting from d-ribose is reported for the first total synthesis of (+)-pseudonocardide A, (+)-pseudonocardide C, and an epimer of ent-pseudonocardide D. The synthesis features a highly Z-selective Wittig olefination, one-pot formation of gamma-butyrolactone and gamma-butenolide through [1,4] O-to-O silyl migration followed by lactonization and an intramolecular oxa-Michael reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Nazar Dovhaniuk, Oleksandr P. Blahun, Bohdan Sosunovych, Mykhailo O. Redka, Bohdan V. Vashchenko, Oleksandr O. Grygorenko
Summary: A new and efficient method for synthesizing licochalcone C in good yield has been developed, involving directed ortho-metalation for regioselective C-prenylation, metalation-formylation, selective O-deprotection, methylation, and aldol reaction. The synthesis of structurally related retrochalcones licoagrochalcones B, C, and D was also proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Akinobu Kamiya, Yuichiro Kawamoto, Toyoharu Kobayashi, Hisanaka Ito
Summary: The first total synthesis of tricyclic diterpenoid callilongisin B from Callicarpa longissima was achieved through a series of selective reactions, including 1,4-addition, allylation, oxidation, intramolecular aldol reaction, and lactonization. These steps collectively lead to the construction of the target compound's structure.
Article
Chemistry, Multidisciplinary
Feng Yang, John A. o Porc
Summary: We report the first asymmetric total syntheses of asnovolins, DMOA-derived spiromeroterpenoids, which are a unique natural product family with attractive structures, unconventional stereochemistry, and potent biological activities. The efficient assembly of the spirocyclic skeleton and establishment of unusual stereochemistry were achieved through specific reaction sequences. Core modifications enabled the synthesis of five asnovolin-related natural products. This study demonstrates the utility of anionic fragment coupling and provides a foundation for the synthesis of spiromeroterpenoid congeners with higher oxidation states.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Hongbin Zhai, Zhenhua Wang, Kewei Chen, Tian-Yu Sun, Jian Wei, Yun-Dong Wu
Summary: The first asymmetric total synthesis of indole alkaloid arbophyllidine has been achieved, featuring key reactions such as intramolecular reductive Heck reaction, Fischer indolization, and oxidative lactonization. Density functional theory calculations were employed to provide a comprehensive understanding of the oxidative lactonization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Applied
Cairong Wang, Ge Qiu, Chen Li, Kai Sun, Zhichuan Wang, Xin Wang
Summary: Carboxylic acid compounds are important structural units that exist widely in nature, and decarboxylative reactions have great significance in synthetic chemistry due to the non-flammable, non-toxic, and easy-to-remove byproduct carbon dioxide. Heterocyclic compounds are important backbones of various biologically active molecules, making research on new synthetic tactics for heterocyclic derivatives based on decarboxylative cyclization of great interest.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Haidi Yang, Jinyao Liu, Pan Hu, Liang Gao, Zedu Huang, Fener Chen
Summary: A new and highly stereoselective synthesis of chiral diol (S)-14, the common synthetic intermediate to (+)-(2R,4 ' R,8 ' R)-alpha-tocopherol (1), was achieved. The method involved a lipase-catalyzed desymmetric hydrolysis reaction, leading to the efficient enzymatic desymmetric synthesis of the chiral chroman skeleton of vitamin E members. Coupled with the modified preparation of the phytol-derived side chain, the chemoenzymatic total synthesis of 1 was completed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hong-Gang Cheng, Zhenjie Yang, Ruiming Chen, Liming Cao, Wen-Yan Tong, Qiang Wei, Qingqing Wang, Chenggui Wu, Shuanglin Qu, Qianghui Zhou
Summary: A concise total synthesis of (-)-berkelic acid is reported in eight linear steps, featuring a Catellani reaction/oxa-Michael cascade, a one-pot deprotection/spiroacetalization operation, and a late-stage Ni-catalyzed reductive coupling. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process, supported by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Long Min, Li-Ping Zhong, Chuang-Chuang Li
Summary: Steroids continue to play a significant role in organic chemistry, medicinal chemistry, and drug discovery. However, the synthesis of unusual rearranged steroids, particularly abeo-steroids with a medium-sized ring, remains a challenge. This Account summarizes the laboratory's efforts in the total synthesis of abeo-steroids using cycloaddition strategies, highlighting the efficiency and versatility of each strategy in constructing structurally complex abeo-steroid cores. The findings provide valuable insights for advancing the total synthesis of abeo- and related steroids.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
K. C. Nicolaou, Ruocheng Yu, Zhaoyong Lu, G. Fernando Alvarez
Summary: Researchers have successfully synthesized a complex natural tropolonoid compound, gukulenin B, which is a challenging target for synthesis. They used a series of site-selective aromatic C-H bond functionalizations and C-C bond formations to successfully construct the tropolone nucleus. This study is of great significance for further synthesis and biological research, and provides new insights for the development of tropolone functionalization methods.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Deepak Saini, Praveen Kumar, Rodney A. Fernandes
Summary: A concise stereoselective total synthesis of two diastereomeric obolactones and 7 ',8 '-dihydroobolactones was achieved, establishing the structure and absolute configuration of these compounds for the first time.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Takayuki Ohyoshi, Hidetada Iizumi, Shu Hosono, Hikaru Tano, Hideo Kigoshi
Summary: The total synthesis of aplysiasecosterols A and B has been accomplished. Key features of the synthesis include the Suzuki-Miyaura coupling of each AB-ring segment and common D-ring segment. This late-stage convergent synthesis, which has rarely been reported in secosteroid synthesis, can be adapted to many 9,11-secosteroids.
Article
Chemistry, Organic
Si-Qing Wang, Wei-Yi Qi, Xue-Song Yin, Bing-Feng Shi
Summary: This paper presents a concise formal total synthesis of (+/-)-7-deoxycylindrospermopsin in 14 steps from commercially available 4-methoxypyridine, with key steps including the elaboration of densely functionalized piperidine, Sonogashira coupling to attach the pyrimidine moiety, and intramolecular conjugate addition of guanidine with alkyne to form the C ring. The synthesis of its 8-epi isomer was also achieved following the same synthetic strategy.
ORGANIC CHEMISTRY FRONTIERS
(2021)
