Article
Chemistry, Multidisciplinary
Rodney A. Fernandes, Dnyaneshwar A. Gorve, Amit K. Jha
Summary: A stereodivergent protecting-group-directed Tsuji-Trost cyclization has been successfully used to synthesize both 2,5-cis- and 2,5-trans-disubstituted-THF scaffolds. In the presence of a beta-O-silyl group, cis-2,5-disubstituted-3-oxygenated THF is formed with a high diastereomeric ratio of up to 9:1. Alternatively, when the free OH at the beta-position can coordinate with acetate, trans-2,5-disubstituted-3-hydroxy THF scaffold is generated as a single diastereomer (diastereomeric ratio up to 1:0). These THF scaffolds were used in the total synthesis of oxylipids and (+)-petromyroxol.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xiwu Zhang, Yuan Wang, Peng Chen, Xinxian Cai, Yanxing Jia
Summary: The total synthesis of (-)-pallambins A-D was successfully achieved by simulating the biosynthetic pathway, efficiently constructing the left and right parts of the compounds. During the process, novel methods such as CH3Li-mediated conversion and a palladium-catalyzed dehydrobromination were discovered, highlighting the importance of highly selective transformations in avoiding protection-group manipulations.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Shogo Kamo, Akihiko Kasamatsu, Junya Shiraiwa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this report, the first total synthesis of (-)-boscartin A, a cembranoid with a 5/5/12-fused tricyclic structure, was described. (-)-Boscartin A was obtained in three steps from (-)-boscartin F, with an overall yield of 46%, utilizing key reactions including stereoselective epoxidation and Wharton reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Adisak Thanetchaiyakup, Hassayaporn Rattanarat, Sudaporn Aree, Tanwawan Duangthongyou, Tanin Nanok, Nutthawat Chuanopparat, Paiboon Ngernmeesri
Summary: Melotenine A, derived from Melodinus tenuicaudatus, shows significant anticancer activity against several human cancer cell lines. The synthesis of (+/-)-melotenine A was achieved in 11 steps with an overall yield of 6.7%, using key steps including a Diels-Alder reaction and ring-closing metathesis.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Shengling Xie, Chengqing Ning, Qingzhen Yu, Jieping Hou, Jing Xu
Summary: This study presents a concise, protecting-group-free total synthesis of cabucine oxindole A, a putative natural spirooxindole alkaloid, and investigates the biological activity of its synthetic intermediates.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Review
Polymer Science
Yihuan Liu, Fan Yin, Xin Hu, Ning Zhu, Kai Guo
Summary: The review summarized the methods of non-metal and metal catalytic unprotected mercapto-alcohol initiating ring-opening polymerization, emphasizing the advantages of using flow chemistry. The remaining challenges and opportunities for the development of thiol-polymer synthesis and applications were discussed.
Article
Chemistry, Organic
Ajay Sharma, Satyendra Kumar Pandey
Summary: An efficient and concise organocatalyzed protecting-group free synthetic approach is described for synthesizing the stereoisomers of the antidepressant drug reboxetine. The synthesis involves organocatalytic Jorgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Patrick Zimdars, Yuzhou Wang, Peter Metz
Summary: A concise and effective total synthesis of (-)-salvinorin A was achieved with high enantioselectivity and diastereoselectivity, using catalytic asymmetric propargylation and substrate-controlled reactions. The synthesis involved intramolecular Diels-Alder reactions and chemoselective Mitsunobu inversion, resulting in a streamlined reaction sequence with only 16 steps and 1.4% total yield. Additionally, an alternative strategy with a 2-bromo-1,3-diene moiety was explored.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Bo-Wei Zhao, Liu Yang, Cheng-Yu Long, Han-Lu Li, Yu-Ting He, Xue-Qiang Wang
Summary: In this study, a Ni-catalyzed coupling strategy for the synthesis of diphenic acid derivatives was developed, and these acids were then used in the synthesis of Pt(II) agents.
Article
Chemistry, Organic
Mainak Bera, Biswajit Sen, Sujay Garai, Saumen Hajra
Summary: In this study, a short and efficient catalytic asymmetric synthesis of dibenzylbutyrolactone lignans was described. Various compounds, including (-)-hinokinin, (-)-yatein, (-)-bursehernin, (-)-pluviatolide, and their 7-hydroxylignans, were successfully synthesized. The method involved organocatalytic aldol-reduction-lactonization and Pd/C-catalyzed hydrogenative debromination reactions, which allowed for a streamlined synthesis with high selectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: Herein, the first total synthesis of (+)-alterbrassicicene C (2) is reported. Key features of this synthesis include an oxiranium mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and the installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: This article describes the first total synthesis of (+)-alterbrassicicene C (2). Key features of the synthesis include an oxiranium-mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Cheng-Yu Long, Hao Chen, Cheng Ma, Bo-Wei Zhao, Shen-Huan Li, Yue Cui, Xinge Yang, Shao-Fei Ni, Xue-Qiang Wang
Summary: A Ni-catalyzed protecting-group-free C-C coupling protocol has been developed for the efficient synthesis of 2,2'-biphenol derivatives. This newly developed strategy demonstrates remarkable chemoselectivity control ability, wide substrate scope, and excellent functional group tolerance.
Article
Chemistry, Organic
Huidan Geng, Fei Chen, Yonglong Zhao, Bing Guo, Lei Tang, Yuan -Yong Yang
Summary: A protecting-group-free method was developed for the diversification of Meridianin alkaloid in a time and step efficient manner. A wide range of substituents were successfully incorporated, leading to moderate to high product yields and the first synthesis of Meridianin B. This simple method enables the rapid construction of a Meridianin derivative library for antibiofilm evaluation. Preliminary results demonstrate the ability of Meridianin derivatives to inhibit Acinetobacter baumannii biofilms and synergistically lower the antibiotic MIC.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huidan Geng, Fei Chen, Yonglong Zhao, Bing Guo, Lei Tang, Yuan-Yong Yang
Summary: A protecting-group-free protocol was developed for the efficient diversification of the Meridianin alkaloid, leading to the synthesis of Meridianin B. The protocol tolerates a broad range of substituents, resulting in moderate to high product yields. Furthermore, preliminary studies demonstrate the potential of Meridianin derivatives in inhibiting Acinetobacter baumannii biofilm and enhancing antibiotic efficacy.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Akihiko Kasamatsu, Motoi Kuwabara, Akinobu Matsuzawa, Kazuyuki Sugita
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Naoto Okutomi, Akinobu Matsuzawa, Kazuyuki Sugita
CHEMISTRY-AN ASIAN JOURNAL
(2019)
Article
Chemistry, Organic
Rintaro Matsuo, Ayumu Miyashita, Motoi Kuwabara, Shinya Adachi, Akinobu Matsuzawa, Kazuyuki Sugita
Article
Chemistry, Organic
Motoi Kuwabara, Ami Matsuo, Shogo Kamo, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: This paper describes the synthesis of the carbon skeleton of cotylenin A aglycone, achieved through key reactions including intramolecular aldol reaction, aldol coupling reaction, and ring-closing meta-thetasis. The stereochemistry was confirmed through single-crystal X-ray crystallographic analyses of related compounds.
SYNTHESIS-STUTTGART
(2021)
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)
Article
Chemistry, Organic
Shogo Kamo, Hitomi Kurosawa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: This study presented a successful eight-step enantioselective synthesis of (-)-lamellodysidine A, a sesquiterpene natural product with a unique tetracyclic skeleton, obtained from a marine sponge. The key to this synthesis is a cascade reaction involving an intramolecular Diels-Alder reaction, and the stereochemistry and absolute configuration were confirmed through single-crystal X-ray crystallography.
Article
Chemistry, Organic
Eiji Nagata, Hisaaki Sakate, Takaharu Okada, Shinya Adachi, Shogo Kamo, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this article, the synthesis of (+/-)-5-epi-vetiverianine A is reported. Key reactions including a rhodium-catalyzed coupling reaction and an oxidative phenolic cyclization enable efficient and stereoselective access to (+/-)-5-epi-vetiverianine A in 11 steps, with an overall yield of 20%. The stereochemistry is confirmed through NOE studies.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Shogo Kamo, Akihiko Kasamatsu, Junya Shiraiwa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this report, the first total synthesis of (-)-boscartin A, a cembranoid with a 5/5/12-fused tricyclic structure, was described. (-)-Boscartin A was obtained in three steps from (-)-boscartin F, with an overall yield of 46%, utilizing key reactions including stereoselective epoxidation and Wharton reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tomoya Mashiko, Yuta Shingai, Jun Sakai, Shinya Adachi, Akinobu Matsuzawa, Shogo Kamo, Kazuyuki Sugita
Summary: The total syntheses of (+)-ganocin A and (-)-cochlearol B, featuring pentacyclic skeletons, in optically active forms, were reported. Key steps such as asymmetric Corey-Bakshi-Shibata reduction, phenolic oxidative cyclization, intramolecular radical cyclization-benzylic oxidative cyclization sequence, and intramolecular [2 + 2] photocycloaddition were utilized, enabling enantioselective access with a longest linear sequence of 17 steps and 9% overall yield for (+)-ganocin A and with 16 steps and 9% overall yield for (-)-cohlearol B.
Article
Chemistry, Organic
Kazuki Hori, Shogo Kamo, Kazuyuki Sugita
Summary: In this study, total syntheses of four Ganoderma-derived meroterpenoids were reported. A flexible approach was developed to construct the 3-alkyl-5-aryl-gamma-butenolide skeleton, a common motif of these meroterpenoids. The target compounds were synthesized with enantioselective access and moderate overall yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Tomoya Mashiko, Eiji Nagata, Hisaaki Sakate, Shogo Kamo, Kazuyuki Sugita
Summary: The first total synthesis of (+)-ent-vetiverianine A, which has a 5/6/6-fused tricyclic structure, is described in this study. Key reactions such as Lewis acid-mediated cyclization, Mukaiyama hydration, enantioselective Shi epoxidation, Birch reduction, and other transformations were utilized, leading to an enantioselective access to (+)-ent-vetiverianine A in 14 steps with an overall yield of 12%.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Rintaro Matsuo, Ayumu Watanabe, Shogo Kamo, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: This study describes the concise total syntheses of Peniclillium sesquiterpenes (+/-)-Penicibilaenes A and B, achieved through efficient intramolecular aldol condensation, stereoselective rhodium-catalyzed 1,4-addition, ring-closing metathesis, and effective transformations. The longest linear sequences for the synthesis of (+/-)-penicibilaenes A and B are 12 and 13 steps, with an overall yield of 4.0% for both compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Tomoya Mashiko, Yuta Nakazato, Yuta Katsumura, Akihiko Kasamatsu, Shinya Adachi, Shogo Kamo, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: The first total synthesis of corallocin A was achieved with high stereoselectivity and good yield using the Suzuki coupling reaction as a key step. Robust transformations including Vilsmeier-Haack formylation and Wittig reaction were utilized for effective access to corallocin A.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shogo Kamo, Hitomi Kurosawa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this study, an eight-step enantioselective synthesis of (-)-lamellodysidine A was achieved. The key to the synthesis is a cascade reaction that includes an intramolecular Diets-Alder reaction. Single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A confirmed the proposed stereochemistry and absolute configuration.
