Chemical and Pharmaceutical Bulletin p. 197 - 203 (1994)
Update date:2022-08-05
Topics:
Isobe
Mohri
Takeda
Suzuki
Hosoi
Tsuda
Oxidation of 8-oxoerythrinan and 8-oxo-1,7-cycloerythrinan derivatives with 2 mol eq of ceric ammonium nitrate in alcohols or acetic acid gave the corresponding 11β-alkoxy or acetoxy compounds in moderate yield. Thus, (±)- 3,3,15,16-tetramethoxy-1,7-cycloerythrinan-2,8-dione and (+)-erysotramidine gave the corresponding 11β-methoxy and 11β-acetoxy derivatives on oxidation in methanol and in acetic acid, respectively. Those compounds were respectively converted into (±)-erythristemine and (+)-erythrartine in several steps, thus achieving the total synthesis of these alkaloids.
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Doi:10.1248/cpb.27.688
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