A new convenient route to 2-oxoethoxycoumarins: key intermediates in the synthesis of natural products

被引:35
作者
Chimichi, S
Boccalini, M
Cosimelli, B
机构
[1] CNR, Ctr Chim & Struttura Composti Eterociclici Loro A, I-50019 Sesto Fno, Firenze, Italy
[2] Dipartimento Chim Organ U Schiff, I-50019 Sesto Fno, Firenze, Italy
[3] Dipartimento Chim Organ A Mangini, I-40127 Bologna, Italy
关键词
hydroxycoumarins; coumarinyloxyaldehydes; Rosenmund reductions; natural product precursors;
D O I
10.1016/S0040-4020(02)00442-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthetic route to coumarinyloxyaldehydes starting from hydroxycoumarins is presented; these compounds, useful intermediates in the preparation of natural products such as geiparvarin and psoralens, are now available in excellent yields with a simple workup procedure. Moreover the reported route has been applied to dihydroxycoumarins. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4851 / 4858
页数:8
相关论文
共 13 条
[1]  
AFFROSSMAN S, 1963, J CHEM SOC, P2024
[2]  
ANTONELLO C, 1958, GAZZ CHIM ITAL, V88, P415
[3]   A NOVEL NONIONIC HYDROGEL FROM 2-METHYL-2-OXAZOLINE .3. POLYOXAZOLINE HAVING A COUMARIN MOIETY AS A PENDANT GROUP - SYNTHESIS AND PHOTOGELATION [J].
CHUJO, Y ;
SADA, K ;
SAEGUSA, T .
MACROMOLECULES, 1990, 23 (10) :2693-2697
[4]   PSORALENES .3. CYCLIZATION STUDIES OF CERTAIN SUBSTITUTED COUMARINS AND COUMARANS [J].
ESSE, RC ;
CHRISTENSEN, BE .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1565-1569
[5]  
HORII Z, 1939, J PHARM SOC JAPAN, V59, P201
[6]   SYNTHESIS AND CONFIGURATIONAL ASSIGNMENT OF GEIPARVARIN - A NOVEL ANTI-TUMOR AGENT [J].
JERRIS, PJ ;
SMITH, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (03) :577-585
[7]   The first direct transformation of 2,2′-dihydroxychalcones into coumestans [J].
Kamara, BI ;
Brandt, EV ;
Ferreira, D .
TETRAHEDRON, 1999, 55 (03) :861-868
[8]  
MASSARANI E, 1963, FARMACO, V18, P254
[9]  
NAKAYAMA H, 1991, Patent No. 0348674
[10]  
PHADKE CP, 1986, SYNTHESIS-STUTTGART, P413