- 著者
- 田之口 真理子 加島 竜彦 雑賀 英之 井上 大志 有本 正生 山口 秀夫
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.37, no.1, pp.68-72, 1989-01-25 (Released:2008-03-31)
- 参考文献数
- 31
- 被引用文献数
- 11 16
Two new lignans, hernolactone (1) and fernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in recemic forms. Firstly, (±)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups. Synthesis of 2 was pursued using the corresponding 4-phenyl-1, 2-dihydronaphthalene lactone(18). The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22). Subsequent hydrogenation of 22 followed by acidification with concetrated hydrochloric acid gave isopicrobernanadin (21), leaving the 2, 3-trans, 3, 4-cis hydroxy acid (23), which was lactonized by means of N, N-dicyclohexylcarbodiimide to afford (±)-2.
- 著者
- 加島 竜彦 田ノ口 真理子 有本 正生 山口 秀夫
- 出版者
- 公益社団法人日本薬学会
- 雑誌
- Chemical & pharmaceutical bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.39, no.1, pp.192-194, 1991-01-25
(±)-Desoxypodophyllotoxin (2), a chief component of the seeds of Hernandia ovigera L., and (±)-β-peltatin-A methyl ether (3), an analogous phenyltetralin lignan, which have 2,3-trans, 3,4-cis configuration were synthesized according to the method developed for the synthesis of hernandin (1). The syntheses were pursued using the corresponding 4-phenyl-1,2-dihydronaphthalene lactones (9 and 10) followed by cleavage of the lactone moiety to give the unsaturated hydroxy acids (11 and 12). Subsequent hydrogenation and ring closure by means of p-toluenesulfonic acid afforded both 2,3-trans, 3,4-cis and 2,3-cis, 3,4-cis ligans (2 and 13 or 3 and 14), which were isolated by preparative thin layer chromatography.