Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions.
The 4-oxofurofuran lignan, (+)-aptosimon (1), was synthesized from gamma-butyrolactone (9). To construct the two benzylic chiral center of (+)-aptosimon (1), highly erythro selective aldol condensation and stereoconvergent SN1 intramolecular cyclization were used as the key reactions.
Yamauchi
Satoshi
S
College of Agriculture, Ehime University, Tarumi 3-5-7, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp
Yamaguchi
Munetoshi
M
D015107:4-Butyrolactone / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis; D003500:Cyclization; D004149:Dioxoles / Q000138:chemical synthesis; D005663:Furans / Q000138:chemical synthesis; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D004149:Dioxoles; D005663:Furans; D017705:Lignans; C476811:aptosimon; D015107:4-Butyrolactone