A concise route to the C2-symmetric tricyclic skeleton of ryanodine

被引：19

作者：

Hagiwara, Koji ^{[1
,2
]}

Himuro, Masafumi ^{[2
]}

Hirama, Masahiro ^{[2
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Bunkyo Ku, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 09期

关键词：

Ryanodine; Dearomatization; Diels-Alder reaction; King expansion; Transannular cyclization; Samarium iodide; MEDIUM-SIZED RINGS; ENOL ETHERS; MERRILACTONE; OXIDATION; CHEMISTRY;

D O I：

10.1016/j.tetlet.2008.12.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ryanodine is a potent calcium channel modulator. In this Letter, we report the 10-step synthesis of the highly substituted tricyclic ring system of ryanodine. Diels-Alder reaction via dearomatization of 2, 5-dimethylbenzene-1,4-diol and subsequent Sml(2)-mediated reductive coupling of eight-membered 1,5-diketone efficiently introduced the four consecutive fully substituted carbons of the tricyclo[3.3.2.0(2,6)]decane system. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1035 / 1037

页数：3

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