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ID 34213
フルテキストURL
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著者
Abe, Hitoshi Okayama University
Takeda, Shigemitsu Okayama University
Fujita, Takuro Okayama University
Nishioka, Keisuke Okayama University
Takeuchi, Yasuo Okayama University Kaken ID
Harayama, Takashi Okayama University
抄録

A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed. Stegane and related compounds are important because of their interesting biological activities such as antileukemic properties.1 One of the most outstanding features of their chemical structures is an unsymmetrical 2,2’-disubstituted biphenyl moiety with an axial chirality (Figure 1). For the formation of such a biphenyl part in the syntheses of the stegane families, several approaches have been attempted such as photocyclization,2 Suzuki coupling,3 oxidative biaryl coupling,4 the SNAr reaction,5 Ullmann coupling,6 and the [2+2+2] three-component cyclization reaction.7

キーワード
steganone
palladium
phenyl benzoate
lactone concept
biary
備考
Digital Object Identifier:10.1016/j.tetlet.2004.01.086
Published with permission from the copyright holder. This is the author's copy, as published in Tetrahedron Letters, March 2004, Volume 45, Issue 11, Pages 2327-2329.
Publisher URL:http://dx.doi.org/10.1016/j.tetlet.2004.01.086
Direct access to Thomson Web of Science record
Copyright © 2004 Elsevier Ltd. All rights reserved.
発行日
2004-3
出版物タイトル
Tetrahedron Letters
45巻
11号
開始ページ
2327
終了ページ
2329
資料タイプ
学術雑誌論文
言語
English
査読
有り
DOI
Web of Science KeyUT
Submission Path
organic_chemistry/1