Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate

Autor: Nunes, R. L., Bieber, L. W., Longo, R. L.
Zdroj: Journal of Natural Products; December 27, 1999, Vol. 62 Issue: 12 p1643-1645, 3p
Abstrakt: 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.
Databáze: Supplemental Index