241149-19-9Relevant academic research and scientific papers
Synthesis of espicufolin based on 6-endo ring closure of o-alkynoylnaphthols
Uno, Hidemitsu,Sakamoto, Katsuji,Honda, Erina,Fukuhara, Kaori,Ono, Noboru,Tanaka, Junya,Sakanaka, Masahiro
, p. 229 - 238 (2007/10/03)
Regioselective halogenation of 3-acetoxymethyl-7-chloro-5,8-dimethoxy-1-naphthol 5 was achieved by DBH or I2/N-methylmorpholine to give the corresponding 2-halogeno-1-naphthols 8 and 11, which were converted to 1-methoxymethoxy-3-(alk-2-ynoyloxymethyl)-2-halogenonaphthalenes 17 and 18 in good yields. An intramolecular acyl-transfer reaction of the 2-halogenonaphthalenes triggered by halogen-lithium exchange with BuLl at -78 °C gave 1-methoxymethoxy-2-alkynoyl-3-(hydroxymethyl)naphthalenes 21 in high yields. After protection of the hydroxymethyl group as a benzoate, formation of a γ-pyrone ring was easily achieved by deprotection of the methoxymethyl group followed by spontaneous 6-endo ring closure under mildly acidic conditions. The pyrone derivative having a 1-methylpropyl group was successfully converted to espicufolin 1.
Total synthesis of (S)-espicufolin and absolute structure determinaton of espicufolin
Uno, Hidemitsu,Sakamoto, Katsuji,Honda, Erina,Ono, Noboru
, p. 1005 - 1006 (2007/10/03)
(S)-Espicufolin was synthesized from 1,4-dimethoxybenzene in 16 steps via an intramolecular acyl-transfer reaction as the key step; the absolute stereochemistry at the 14-position of natural espicufolin was determined to be R.
