199612-65-2Relevant academic research and scientific papers
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.
Synthesis of the benzo[b]fluorene core of the kinamycins by arylalkyne-allene and arylalkyne-alkyne cycloadditions
Gonzalez-Cantalapiedra, Esther,De Frutos, Oscar,Atienza, Carmen,Mateo, Cristina,Echavarren, Antonio M.
, p. 1430 - 1443 (2007/10/03)
Arylalkyne-allene and arylalkyne-alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne-alkyne cycloadditions, we found a rearrangement that produces benzo-[a]fluorenones, in addition to the expected benzo[b]fluorenones. This rearrangement could be suppressed in the presence of phenol, which allowed the synthesis of 4,9-dimeth-oxy-2-methyl-11H-benzo[b] fluoren-11-one in excellent yield. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
An intramolecular arylation route to the kinafluorenones
Qabaja, Ghassan,Jones, Graham B.
, p. 5317 - 5320 (2007/10/03)
Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of kinafluorenone 2, providing an effective alternative to Friedel-Crafts-based approaches. (C) 2000 Elsevier Science Ltd.
Annulation strategies for benzo[b]fluorene synthesis: efficient routes to the kinafluorenone and WS-5995 antibiotics.
Qabaja,Jones
, p. 7187 - 7194 (2007/10/03)
Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative to Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also 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 analogues was demonstrated, and antitumoral activity of this class was determined.
