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.

引用

页码：8383 / 8386

页数：4

共 34 条

[1] Mechanistic study of the Mitsunobu reaction
Ahn, CJ
Correia, R
DeShong, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) : 1751 - 1753
[2] An approach to the stereoselective synthesis of syn- and anti-1,3-diol derivatives.: Retention of configuration in the Mitsunobu reaction
Ahn, CJ
DeShong, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) : 1754 - 1759
[3] Chemoselective esterification of phenolic acids and alcohols
Appendino, G
Minassi, A
Daddario, N
Bianchi, F
Tron, GC
[J]. ORGANIC LETTERS, 2002, 4 (22) : 3839 - 3841
[4] Coumarins and anti-HBV constituents from Zanthoxylum schinifolium
Chang, CT
Doong, SL
Tsai, IL
Chen, IS
[J]. PHYTOCHEMISTRY, 1997, 45 (07) : 1419 - 1422
[5] Cravotto G, 2003, SYNTHESIS-STUTTGART, P1286
[6] 4-hydroxycoumarin and related systems: Sitoselectivity of the Mitsunobu reaction with prenyl alcohols
Cravotto, G
Nano, GM
Palmisano, G
Tagliapietra, S
[J]. HETEROCYCLES, 2003, 60 (06) : 1351 - 1358
[7] Dehydrative alkylation of alcohols with triethyl methanetricarboxylate under Mitsunobu conditions
Cravotto, G
Giovenzana, GB
Sisti, M
Palmisano, G
[J]. TETRAHEDRON, 1996, 52 (40) : 13007 - 13016
[8] CRAVOTTO G, 2002, 28 C NAZ SCI ROM, pP95
[9] Synthesis of collinin, an antiviral coumarin
Curini, M
Epifano, F
Maltese, F
Marcotullio, MC
Gonzales, SP
Rodriguez, JC
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (01) : 59 - 60
[10] BACTERIAL CAROTENOIDS .48. TOTAL SYNTHESES OF CAROTENES OF 1,2-DIHYDRO SERIES
EIDEM, A
BUCHECKER, R
KJOSEN, H
LIAAENJENSEN, S
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (10): : 1015 - 1023

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