Synthesis of a tetracyclic substructure of Manzamine A via the Diels-Alder reaction of dihydropyridinones

被引：28

作者：

Torisawa, Y ^{[1
]}

Hosaka, T ^{[1
]}

Tanabe, K ^{[1
]}

Suzuki, N ^{[1
]}

Motohashi, Y ^{[1
]}

Hino, T ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] CHIBA UNIV,FAC PHARMACEUT SCI,INAGE KU,CHIBA 263,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 32期

关键词：

D O I：

10.1016/0040-4020(96)00607-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the tetracyclic core (19) of manzamine A (I) was achieved via Diels-Alder reaction of the dihydropyridinones (5, 6). Conversion of the two D-A products (7, 8) to the key tricyclic ketone (10) was conducted through a conventional pathway (Scheme Ill) as well as a new pathway developed (Scheme IV). For effective construction of the required azocine ring systems, model studies were carried out to find intramolecular amide formation by pentafluorophenyl ester and DPPA methods, which were successfully applied to the real substrate refurnish the titled core structure (19). Copyright (C) 1996 Elsevier Science Ltd

引用

页码：10597 / 10608

页数：12

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