5090-88-0Relevant academic research and scientific papers
Lipase-catalyzed site-selective deacetylation of sterically hindered naphthohydroquinone diacetate and its application to the synthesis of a heterocyclic natural product
Hanaya, Kengo,Hashimoto, Riichi,Higashibayashi, Shuhei,Sakakura, Ayaka,Sugai, Takeshi
, p. 625 - 632 (2019/08/01)
Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-l,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the a-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.
Synthesis of mansonone F based on the regioselective hydrolysis of a hydroquinone diacetate
Nunes, Ruth L.,Bieber, Lothar W.,Longo, Ricardo L.
, p. 1643 - 1645 (2007/10/03)
The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl- 1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.
Intramolecular Diels-Alder Additions of Benzynes to Furans. Application to the Total Synthesis of Biflorin, and the Mansonones E, I, and F
Best, Wayne M.,Wege, Dieter
, p. 647 - 666 (2007/10/02)
Benzynes, generated either by the debromination of an appropriately substituted o-dibromobenzene, or by the thermolysis of a substituted diazotized anthranilic acid, have been trapped intramolecularly by an attached furan moiety.One such adduct (41) has b
