135678-35-2Relevant academic research and scientific papers
Synthesis of arizonin C1
Brimble, Margaret A.,Phythian, Sara J.,Prabaharan, Hishani
, p. 2855 - 2860 (2007/10/02)
The first syntheses of the pyranonaphthoquinone antibiotics 5-epi-arizonin B1 16, 5-epi-arizonin C1 15 and arizonin C1 3 are described.The key steps involve addition of 2-trimethylsilyloxyfuran 12 to the 2-acetylnaphthoquinone 11 affording the adduct 13 which undergoes oxidative rearrangement to a pyranonaphthoquinone system 14 upon treatment with ceric ammonium nitrate.The regioselective synthesis of naphthoquinone 11 via oxidation of ketone 10 is described wherein 10 is prepared via addition of furan to 3,4-dimethoxydehydrobenzene followed by treatment with acid.
Regioselectivity in the Reactions of Methoxydehydrobenzenes with Furans. Part 2. 2-Methoxyfuran and Methoxydehydrobenzenes
Giles, Robin G. F.,Hughes, Andrew B.,Sargent, Melvyn V.
, p. 1581 - 1587 (2007/10/02)
Acid-induced ring opening of adducts of furan and methoxydehydrobenzenes gives the naphthalenols derived from the more stable carbocation.The cycloadditions of methoxydehydrobenzenes containing a 3-methoxy group and 2-methoxyfuran are highly regiospecific
