Divergent synthesis of withasomnines via synthesis of 4-hydroxy-1H-pyrazoles and Claisen rearrangement of their 4-O-allylethers

被引：27

作者：

Ichikawa, Hayato ^{[1
,2
]}

Watanabe, Ryo ^{[1
]}

Fujino, Yuiko ^{[1
]}

Usami, Yoshihide ^{[1
]}

机构：

[1] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan

[2] Nihon Univ, Coll Ind Technol, Chiba 2758575, Japan

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 34期

关键词：

Withasomnine; Pyrazole; Claisen rearrangement; Suzuki coupling; CROSS-COUPLING REACTION; PYRAZOLE ALKALOIDS; ALCOHOL-DEHYDROGENASE; RADICAL CYCLIZATION; 4-HYDROXYPYRAZOLE; INHIBITORS; BARK;

D O I：

10.1016/j.tetlet.2011.06.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Hydroxypyrazoles were synthesized by the alkaline hydrolysis of the Baeyer-Villiger oxidation products of 4-formylpyrazoles. This new synthesis of 4-hydroxypyrazoles was applied to the divergent synthesis of withasomnine alkaloids in a unique strategy, for which the key steps included the regioselective Claisen rearrangement of their 4-O-allyl-4-hydroxy-1H-pyrazoles and a Suzuki coupling of 4-trifluoromethanesulfonyloxy-1H-pyrazoles and arylboronic acids. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4448 / 4451

页数：4

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