6555-40-4Relevant articles and documents
Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro
supporting information, p. 1653 - 1657 (2019/05/29)
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.
Enediyne antitumor antibiotic maduropeptin biosynthesis featuring a C-methyltransferase that acts on a COA-Tethered aromatic substrate
Ling, Jianya,Horsman, Geoffrey P.,Huang, Sheng-Xiong,Luo, Yinggang,Lin, Shuangjun,Shen, Ben
supporting information; experimental part, p. 12534 - 12536 (2010/11/04)
The enediyne antitumor antibiotic maduropeptin (MDP) is produced by Actinomadura madurae ATCC 39144. The biosynthetic pathway for the 3,6-dimethylsalicylic acid moiety of the MDP chromophore is proposed to be comprised of four enzymes: MdpB, MdpB1, MdpB2, and MdpB3. Based on the previously characterized biosynthesis of the naphthoic acid moiety of neocarzinostatin (NCS), we expected a biosynthetic pathway featuring carboxylic acid activation by the MdpB2 CoA ligase immediately before its coupling to an enediyne core intermediate. Surprisingly, the MDP aromatic acid biosynthetic pathway employs an unusual logic in which MdpB2-catalyzed CoA activation occurs before MdpB1-catalyzed C-methylation, demonstrating that MdpB1 is apparently unique in its ability to C-methylate a CoA-tethered aromatic acid. MdpB2 is a promiscuous CoA ligase capable of activating a variety of salicylic acid analogues, a property that could be potentially exploited to engineer MDP analogues.
A novel synthesis of bromomethoxy disubstituted derivatives of benzocyclobutenone
Barve,Schiess
, p. 1729 - 1736 (2007/10/03)
Flash vacuum pyrolysis of ortho-methyl aromatic acid chlorides has been used to prepare a variety of substituted derivatives of the benzocyclobutenone ring system starting from simple precursors. The significance of the present reaction lies in the fact that the bromine atom present in the aromatic nucleus, remains undisturbed during the high temperature treatment employed in the pyrolysis and forms, a bromomethoxyketone successfully. This is an altogether new approach.
