85432-87-7Relevant articles and documents
Total Synthesis of Clavilactones
Takao, Ken-Ichi,Mori, Kento,Kasuga, Kenya,Nanamiya, Ryuki,Namba, Ayumi,Fukushima, Yuuki,Nemoto, Ryuichi,Mogi, Takuma,Yasui, Hiroyuki,Ogura, Akihiro,Yoshida, Keisuke,Tadano, Kin-Ichi
, p. 7060 - 7075 (2018/07/15)
Clavilactones A, B, and D are epidermal growth factor receptor tyrosine kinase inhibitors that were isolated from cultures of the fungus Clitocybe clavipes. Here, we report full details of the total synthesis of these clavilactones. A key feature of our s
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.
Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2
Sato, Kenichiro,Asao, Naoki,Yamamoto, Yoshinori
, p. 8977 - 8981 (2007/10/03)
An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B2, is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone