7473-18-9Relevant articles and documents
Synthesis, biological evaluation, and correlation of cytotoxicity versus redox potential of 1,4-naphthoquinone derivatives
Shen, Chien-Chang,Afraj, Shakil N.,Hung, Chia-Cheng,Barve, Balaji D.,Kuo, Li-Ming Yang,Lin, Zhi-Hu,Ho, Hisu-O.,Kuo, Yao-Haur
supporting information, (2021/04/12)
A series of 1,4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoqui
A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
Yu, Wanwan,Hjerrild, Per,Jacobsen, Kristian M.,Tobiesen, Henriette N.,Clemmensen, Line,Poulsen, Thomas B.
supporting information, p. 9805 - 9809 (2018/07/31)
The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.
Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: Scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C
Ogata, Tokutaro,Yoshida, Tomoyo,Shimizu, Maki,Tanaka, Manami,Fukuhara, Chie,Ishii, Junko,Nishiuchi, Arisa,Inamoto, Kiyofumi,Kimachi, Tetsutaro
, p. 1423 - 1432 (2017/02/15)
A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered easy access to a natural product possessing anti-tumor activity.