Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol

被引：13
作者：
Cravotto, G
Chimichi, S
Robaldo, B
Boccalini, M
机构：
[1] Univ Turin, Dipartimento Sci & Tecnol Farmaco, I-10125 Turin, Italy
[2] Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Florence, Italy
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 46期
关键词：
dihydroxycoumarins monoalkylation; high intensity ultrasound; Mitsunobu dehydroalkylation; ferujol synthesis;
D O I：
10.1016/j.tetlet.2003.09.114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by NOESY experiments; though less selectively, position 7 was also the most reactive in daphnetin (7,8-dihydroxycoumarin). The synthesis of the phytoestrogen ferujol is also reported for the first time. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：8383 / 8386
页数：4
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