Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions.

Satoshi Yamauchi, Munetoshi Yamaguchi

College of Agriculture, Ehime University, Tarumi 3-5-7, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp

Bioscience, biotechnology, and biochemistry 2003 Apr

filter terms:

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.

Citation

Satoshi Yamauchi, Munetoshi Yamaguchi. Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions. Bioscience, biotechnology, and biochemistry. 2003 Apr;67(4):838-46