Efficient synthesis of neurotrophic honokiol using Suzuki-Miyaura reactions

被引:11
作者
Harada, Kenichi [1 ]
Arioka, Chiharu [1 ]
Miyakita, Akina [1 ]
Kubo, Miwa [1 ]
Fukuyama, Yoshiyasu [1 ]
机构
[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima 7708514, Japan
关键词
Honokiol; Neolignan; Suzuki-Miyaura reaction; Neurotrophic activity; CEREBRAL-ISCHEMIA-REPERFUSION; CONCISE SYNTHESIS; CELLS;
D O I
10.1016/j.tetlet.2014.09.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient synthesis of honokiol (1) was accomplished using two kinds of Suzuki-Miyaura reactions. The first Suzuki-Miyaura reaction was employed to couple 2-bromophenol (6) with 4-hydroxyphenylboronic acid (5), giving rise to biphenol 4, and the second coupling was used to introduce allyl groups at 5- and 3'-positions of honokiol. The total synthesis of 1 was completed in 74% yield over five steps from 6, or in 83% yield over four steps from biphenol 4. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6001 / 6003
页数:3
相关论文
共 16 条
[1]   A concise synthesis of honokiol [J].
Chen, Chang-Ming ;
Liu, Yeuk-Chuen .
TETRAHEDRON LETTERS, 2009, 50 (10) :1151-1152
[2]   A concise synthesis of honokiol [J].
Denton, Ross M. ;
Scragg, James T. ;
Galofre, Adria M. ;
Gui, Xiechao ;
Lewis, William .
TETRAHEDRON, 2010, 66 (40) :8029-8035
[3]   Efficient synthesis and structure-activity relationship of honokiol, a neurotrophic biphenyl-type neolignan [J].
Esumi, T ;
Makado, G ;
Zhai, HF ;
Shimizu, Y ;
Mitsumoto, Y ;
Fukuyama, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (10) :2621-2625
[4]   Neurotrophic activity of honokiol on the cultures of fetal rat cortical neurons [J].
Fukuyama, Y ;
Nakade, K ;
Minoshima, Y ;
Yokoyama, R ;
Zhai, HF ;
Mitsumoto, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (08) :1163-1166
[5]   NEUROTROPHIC SESQUITERPENE-NEOLIGNANS FROM MAGNOLIA-OBOVATA - STRUCTURE AND NEUROTROPHIC ACTIVITY [J].
FUKUYAMA, Y ;
OTOSHI, Y ;
MIYOSHI, K ;
NAKAMURA, K ;
KODAMA, M ;
NAGASAWA, M ;
HASEGAWA, T ;
OKAZAKI, H ;
SUGAWARA, M .
TETRAHEDRON, 1992, 48 (03) :377-392
[6]   The bromination of 2-phenylphenyl acetate [J].
Hazlet, SE ;
Kornberg, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :1890-1892
[7]  
Kawai T., 1993, PLANTA MED, P17
[8]   Honokiol protects rat brain from focal cerebral ischemia-reperfusion injury by inhibiting neutrophil infiltration and reactive oxygen species production [J].
Liou, KT ;
Shen, YC ;
Chen, CF ;
Tsao, CM ;
Tsai, SK .
BRAIN RESEARCH, 2003, 992 (02) :159-166
[9]   Magnolol and honokiol prevent learning and memory impairment and cholinergic deficit in SAMP8 mice [J].
Matsui, Nobuaki ;
Takahashi, Kazuki ;
Takeichi, Miho ;
Kuroshita, Touma ;
Noguchi, Kaori ;
Yamazaki, Kana ;
Tagashira, Hideaki ;
Tsutsui, Kenichi ;
Okada, Hideki ;
Kido, Yuki ;
Yasui, Yumiko ;
Fukuishi, Nobuyuki ;
Fukuyama, Yoshiyasu ;
Akagi, Masaaki .
BRAIN RESEARCH, 2009, 1305 :108-117
[10]   A short and efficient synthesis of honokiol via Claisen rearrangement [J].
Reddy, B. V. Subba ;
Rao, R. Nageshwar ;
Reddy, N. Siva Senkar ;
Somaiah, R. ;
Yadav, J. S. ;
Subramanyam, Ravi .
TETRAHEDRON LETTERS, 2014, 55 (05) :1049-1051