Quinolizidines. XX. Racetnic and Chiral Syntheses of the Alangium Alkaloids 9-Demethylprotoemetinol and 10-Demethylprotoemetinol(Organic,Chemical)

フォーマット:

論文

責任表示:

Fujii, Tozo ; Ohba, Masashi ; Ali, Esahak ; Suzuki, Hitoshi ; Sakaguchi, Jun

言語:

英語

出版情報:

日本薬学会, 1987-07-25

著者名:

• Fujii, Tozo
• Ohba, Masashi
• Ali, Esahak
• Suzuki, Hitoshi
• Sakaguchi, Jun

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363      

巻:

35

通号:

7

開始ページ:

2755

終了ページ:

2760

バージョン:

publisher

概要:

The synthesis of (±)-9-demethylprotoemetinol [(±)-3d] was accomplished by LiAlH_4 reduction of the tricyclic ester (±)-5 and subsequent debenzylation of the resulting tricyclic-alcohol (±)-10. Acetylation of (±)-3d with acetic anhydride and pyridine gave the diacetate (±)-11. The same sequence of reactions starting with (-)-5 afforded (-)-9-demethylprotoemetinol [(-)-3d] and the diacetate (-)-11 through … (-)-10. Parallel synthetic routes starting with the isomeric tricyclic esters (±)-9 and (-)-9 produced (±)- and (-)-10-demethylprotoemetinols [(±)-4d and (-)-4d] and the corresponding diacetates [(±)-13 and (-)-13] through (±)-12 and (-)-12, respectively. The correctness of the structure and absolute stereochemistry of an Alangiutn alkaloid inferred to be 10-demethylprotoemetinol was confirmed by a direct comparison of its diacetate with synthetic (-)-13. 続きを見る

URL:

http://hdl.handle.net/2297/7667