119650-45-2Relevant academic research and scientific papers
Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
Lai, Yao-Hsuan,Mondal, Soumik,Su, Hsin-Tzu,Huang, Sheng-Cih,Wu, Mine-Hsine,Huang,Yang Lauderdale, Tsai-Ling,Song, Jen-Shin,Shia, Kak-Shan,Mong, Kwok-Kong Tony
, p. 9426 - 9432 (2021/03/16)
Herein, we report the total synthesis of landomycins Q and R as well as the aglycone core, namely anhydrolandomycinone and a related core analogue. The synthesis features an acetate-assisted arylation method for construction of the hindered B-ring in the
A general strategy for diverse syntheses of anhydrolandomycinone, tetrangulol, and landomycinone
Sie, Cheng-Jhe,Patteti, Venukumar,Yang, Yi-Ru,Mong, Kwok-Kong Tony
supporting information, p. 1885 - 1888 (2018/02/23)
A general synthetic strategy based on a protecting group-promoted CH arylation method was developed for total syntheses of anhydrolandomycinone (1), tetrangulol (2), and landomycinone (3) from the same set of starting materials.
Reactions of [2-(2-Naphthyl)phenyl]acetylenes and 2-(2-Naphthyl)benzaldehyde O-Phenyloximes: Synthesis of the Angucycline Tetrangulol and 1,10,12-Trimethoxy-8-methylbenzo[c]phenanthridine
Ngwira, Kennedy J.,Rousseau, Amanda L.,Johnson, Myron M.,de Koning, Charles B.
, p. 1479 - 1488 (2017/04/01)
The Suzuki–Miyaura coupling reaction between (1,4,5-trimethoxynaphthalen-2-yl)boronic acid and 2-iodo-3-methoxy-5-methylbenzaldehyde gave the intermediate 3-methoxy-5-methyl-2-(1,4,5-trimethoxynaphthalen-2-yl)benzaldehyde. Conversion of this benzaldehyde
Synthesis of a landomycinone skeleton via Masamune-Bergmann cyclization
Yamaguchi, Sho,Tanaka, Hiroshi,Yamada, Ryo,Kawauchi, Susumu,Takahashi, Takashi
, p. 32241 - 32248 (2014/08/18)
In this report, a synthetic study of landomycinone via Masamune-Bergmann cyclization is described. A 10-membered 1,2-dialkynylbenzene derivative was designated as a key intermediate in the formation of an angular tetracyclic core via Masamune-Bergmann cyclization. Cyclization was expected to proceed under mild heating conditions based on a DFT transition state analysis of the 10-membered enediyne. The enediyne was successfully prepared by intramolecular NHK cyclization in good yield and underwent Masamune-Bergman cyclization at 70 °C for 2 h. However, an undesired β-elimination of the secondary alcohol was involved in the cyclization. In addition, iodination at the 12 position did not occur due to the steric hindrance of two methyl groups. This methodology should be widely applicable to the synthesis of various types of highly oxy-functionalized anthraquinone derivatives as well as landomycinone, and should be a useful way to clarify structure-activity relationships. the Partner Organisations 2014.
Total synthesis of isoprekinamycin: Structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells
Liu, Wei,Buck, Matthew,Chen, Nan,Shang, Muhong,Taylor, Nicholas J.,Asoud, Jalil,Wu, Xing,Hasinoff, Brian B.,Dmitrienko, Gary I.
, p. 2915 - 2918 (2008/02/07)
The structurally novel diazobenzo[a]fluorene antibiotic isoprekinamycin (IPK) has been synthesized for the first time employing a Suzuki coupling of a brominated AB ring synthon with a boronate ester representing the D ring, followed by anionic cyclizatio
Regioselective lactonization of naphthoquinones: Synthesis and antitumoral activity of the WS-5995 antibiotics
Qabaja, Ghassan,M. Perchellet, Elisabeth,Perchellet, Jean-Pierre,Jones, Graham B.
, p. 3007 - 3010 (2007/10/03)
An acid promoted quinolactonization of naphthoquinones has been developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS- 5995A, WS-5995C and functional analogs is demonstrated. Preliminary antitumoral activity of the analogs is presented together with electrochemical analysis. (C) 2000 Elsevier Science Ltd.
