Regular Issue

Vol. 29, No. 2, 1989

32 data found. 31 - 32 listedFirst Previous
Paper | Regular issue | Vol 29, No. 2, 1989, pp.397-402
Published online:
DOI: 10.3987/COM-89-4813
■ Sulfur-containing Dioxopiperazine Derivatives from Emericella heterothallica

Nobuo Kawahara, Koohei Nozawa, Shoichi Nakajima, Mikio Yamazaki, and Ken-ichi Kawai*

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Emethacins A (1) and B (2), sulfur-containing dioxopiperazines, were isolated from Emericella heterothallica ATCC 16824, along with three dioxopiperazine derivatives (3-5). Emethacin B was identical with (3R,6R)-3,6-dibenzyl-3,6-bis(methylthio)-2,5-dioxopiperazine (2) which had been already isolated from Asperqillus terreus.The structure of the new compound, emethacin A (1), was confirmed by spectroscopic and chemical correlation as (3R,6R)-3-benzyl-6-benzylidene-3-methylthio-2,5-dioxopiperazine. Compound 3 was (3S, 6Z)-3-benzyl-6-benzylidene-2,5-dioxopiperazine, which was the enantiomer of the compound 7 isolated from Streptomyces noursei.

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Paper | Regular issue | Vol 29, No. 2, 1989, pp.403-409
Published online:
DOI: 10.3987/COM-89-4824
■ Synthesis of 1-Cyano-2-phenyl-1,2,4,5-tetrahydro-3H-3-benzazepines

Kazuhiko Orito,* Hiroshi Suginome, and Russel Rodrigo

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0828, Japan

Abstract

N-(2-cyanmethyl-4,5-methoxyphenethyl) trifluoroacetamides 3, prepared by two step cyanomethylation of N-(3,4-dimethoxyphenethyl) trifluoroacetamides 1, were treated with benzaldehydes in the presence of EtONa to give the titled benzazepines 5. The structures of 5 were elucidated by 1H nmr analysis, and the cyclization mechanism was also described.

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32 data found. 31 - 32 listedFirst Previous