Oxytrofalcatin Puzzle: Total Synthesis and Structural Revision of Oxytrofalcatins B and C

被引:4
作者
Sugitate, Kazuma [1 ]
Yamashiro, Toshiki [1 ]
Takahashi, Ibuki [2 ]
Yamada, Koji [2 ]
Abe, Takumi [1 ]
机构
[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Kita Ku, Okayama 7008530, Japan
[2] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan
关键词
REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; H FUNCTIONALIZATION; OXAZOLES; DESIGN; CYCLIZATION; ANNULATION; INHIBITORS; ALDEHYDES; ANALOGS;
D O I
10.1021/acs.joc.3c00691
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The previously reported structures of oxytrofalcatinsB and C possessa benzoyl indole core. However, following synthesis and NMR comparisonof both the proposed structure and the synthesized oxazole, we haverevised the structure of oxytrofalcatins B and C as oxazoles. Thesynthetic route developed herein can further our understanding ofthe biosynthetic pathways that govern the production of natural 2,5-diaryloxazoles.
引用
收藏
页码:9920 / 9926
页数:7
相关论文
共 44 条
[1]   First Total Synthesis of Reassigned Echinosulfonic Acid D [J].
Abe, Takumi ;
Nakajima, Ren ;
Yamashiro, Toshiki ;
Sawada, Daisuke .
JOURNAL OF NATURAL PRODUCTS, 2022, 85 (08) :2122-2125
[2]   Revisiting 2-Alkoxy-3-bromoindolines: Control C-2 vs. C-3 Elimination for Regioselective Synthesis of Alkoxyindoles [J].
Abe, Takumi ;
Kosaka, Yuta ;
Kawasaki, Takaaki ;
Ohata, Yuki ;
Yamashiro, Toshiki ;
Yamada, Koji .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2020, 68 (06) :555-558
[3]   Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements [J].
Abe, Takumi ;
Kosaka, Yuta ;
Asano, Miku ;
Harasawa, Natsuki ;
Mishina, Akane ;
Nagasue, Misato ;
Sugimoto, Yuri ;
Katakawa, Kazuaki ;
Sueki, Shunsuke ;
Anada, Masahiro ;
Yamada, Koji .
ORGANIC LETTERS, 2019, 21 (03) :826-829
[4]   Concise Syntheses of Hyrtioreticulins C and D via a C-4 Pictet-Spengler Reaction: Revised Signs of Specific Rotations [J].
Abe, Takumi ;
Yamada, Koji .
JOURNAL OF NATURAL PRODUCTS, 2017, 80 (02) :241-245
[5]   Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E [J].
Abe, Takumi ;
Yamada, Koji .
ORGANIC LETTERS, 2016, 18 (24) :6504-6507
[6]   Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity [J].
Arisawa, Mitsuhiro ;
Kasaya, Yayoi ;
Obata, Tohru ;
Sasaki, Takuma ;
Nakamura, Tomonori ;
Araki, Takuya ;
Yamamoto, Koujirou ;
Sasaki, Akito ;
Yamano, Akihito ;
Ito, Mika ;
Abe, Hiroshi ;
Ito, Yoshihiro ;
Shuto, Satoshi .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (18) :8152-8163
[7]   A Green Synthetic Approach towards Polyarylated Oxazoles via Iodine-Catalyzed One-Pot sp3 C-H Functionalization in Water: From Natural Product Synthesis To Photophysical Studies [J].
Banerji, Biswadip ;
Adhikary, Saswati ;
Majumder, Leena ;
Ghosh, Saswati .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (04) :514-525
[8]   Trypanocidal Activity of 2,5-Diphenyloxazoles Isolated from the Roots of Oxytropis lanata [J].
Banzragchgarav, Orkhon ;
Murata, Toshihiro ;
Odontuya, Gendaram ;
Buyankhishig, Buyanmandakh ;
Suganuma, Keisuke ;
Davaapurev, Bekh-Ochir ;
Inoue, Noboru ;
Batkhuu, Javzan ;
Sasaki, Kenroh .
JOURNAL OF NATURAL PRODUCTS, 2016, 79 (11) :2933-2940
[9]   Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases [J].
Bey, Emmanuel ;
Marchais-Oberwinkler, Sandrine ;
Kruchten, Patricia ;
Frotscher, Martin ;
Werth, Ruth ;
Oster, Alexander ;
Alguel, Oztekin ;
Neugebauer, Alexander ;
Hartmann, Rolf W. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (12) :6423-6435
[10]   Petrosamine B, an inhibitor of the Helicobacter pylori enzyme aspartyl semialdehyde dehydrogenase from the Australian sponge Oceanapia sp. [J].
Carroll, AR ;
Ngo, A ;
Quinn, RJ ;
Redburn, J ;
Hooper, JNA .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (05) :804-806