25932-97-2Relevant academic research and scientific papers
The synthesis of 7,9-dimethoxy-3-propyl-3,4-dihydro-1H-benzo[g]isochromene- 1,5,10-trione: A potential monomer for the synthesis of the natural product xylindein
De Koning, Charles B.,Firoj Hossain, Md,Lemmerer, Andreas
, (2020)
A novel synthesis of a 3-propyl-substituted-benzo[g]isochromene quinone, a potential monomer of the natural product xylindein, was accomplished in 9 steps (overall yield of 8.2%) from 2,4- dimethoxybenzaldehyde. Key steps included the use of a cross-metathesis reaction in which ethyl-3-allyl-4- (benzyloxy)-1,6,8-trimethoxy-2-naphthoate was converted into ethyl-4-(benzyloxy)-1,6,8-trimethoxy-3-(4- oxopent-2-enyl)-2-naphthoate as a mixture of (E)- and (Z)-isomers. Following an oxa-Michael addition reaction, a racemic mixture of the desired product, 5-(benzyloxy)-7,9,10-trimethoxy-3-(2-oxopropyl)-3,4- dihydro-1H-benzo[g]isochromen-1-one, the basic xylindein lactone skeleton, was obtained.
The synthesis of the pyranonaphthoquinones dehydroherbarin and anhydrofusarubin using Wacker oxidation methodology as a key step and other unexpected oxidation reactions with ceric ammonium nitrate and salcomine
Pillay, Adushan,Rousseau, Amanda L.,Fernandes, Manuel A.,De Koning, Charles B.
, p. 7809 - 7819 (2013/04/23)
The synthesis of two closely related pyranonaphthoquinones, dehydroherbarin and anhydrofusarubin, is described. The construction of the naphthalene nuclei was achieved using the Stobbe condensation reaction using 2,4- dimethoxybenzaldehyde and 2,4,5-trime
The synthesis of ventiloquinone L, the monomer of cardinalin 3
Mmutlane, Edwin M.,Michael, Joseph P.,Green, Ivan R.,De Koning, Charles B.
, p. 2461 - 2470 (2007/10/03)
Readily available ethyl-4-acetoxy-6,8-dimethoxynaphthalene-2-carboxylate 27 was converted into 1 -[3-allyl-4(benzyloxy)-6,8-dimethoxy-2-naphthyl)-1-ethanol 31 in seven steps. Subjection of this compound to Wacker oxidation conditions provided 5-benzyloxy-
A synthesis of a thysanone analog
Kraus, George A,Ogutu, Herbert
, p. 7391 - 7395 (2007/10/03)
Hemiacetal 10 was prepared in 13 steps from dimethoxybenzaldehyde. Key steps included the salcomine oxidation of a phenol and a selective deprotection using boron trichloride.
