A three-step and enantioselective synthesis of (-)-(S)- or (+)-(R)-2-(furan-3-yl)-3,6-dihydro-2H-pyrans

被引:13
作者
de Rosa, M [1 ]
Solladié-Cavallo, A
Scettri, A
机构
[1] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, SA, Italy
[2] Univ Strasbourg, ECPM, F-67087 Strasbourg 2, France
关键词
furyl-dihydropyranes; asymmetric allylation; ring-closing metathesis;
D O I
10.1016/S0040-4039(99)02337-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically enriched (3-furyl)-2-pyran derivatives, key-intermediates in the synthesis of the pharmacophoric pyranofuranone system of the bioactive natural products manoalide and cacospongionolide B, are easily accessible by a rapid sequence involving a chiral allylation and a ring closing metathesis reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1593 / 1596
页数:4
相关论文
共 12 条
[1]   Efficient synthesis of chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones [J].
De Rosa, M ;
Dell'Aglio, R ;
Soriente, A ;
Scettri, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (19) :3659-3662
[2]   Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues [J].
De Rosa, M ;
Giordano, S ;
Scettri, A ;
Sodano, G ;
Soriente, A ;
Pastor, PG ;
Alcaraz, MJ ;
Payá, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (17) :3232-3238
[3]  
de Silva E.D., 1980, TETRAHEDRON LETT, V21, P1611, DOI [10.1016/S0040-4039(00)77766-5, DOI 10.1016/S0040-4039(00)77766-5]
[4]   Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa [J].
deRosa, S ;
Crispino, A ;
deGiulio, A ;
Iodice, C ;
Pronzato, R ;
Zavodnik, N .
JOURNAL OF NATURAL PRODUCTS, 1995, 58 (11) :1776-1780
[5]  
DESILVA ED, 1970, TETRAHEDRON LETT, V21, P1611
[6]  
Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2923, DOI 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO
[7]  
2-1
[8]  
GRUBBS HR, 1998, J CHEM SOC P1, P371
[9]   CHEMICAL MECHANISM OF INACTIVATION OF BEE VENOM PHOSPHOLIPASE-A2 BY THE MARINE NATURAL-PRODUCTS MANOALIDE, LUFFARIELLOLIDE, AND SCALARADIAL [J].
POTTS, BCM ;
FAULKNER, DJ ;
DECARVALHO, MS ;
JACOBS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5093-5100
[10]   CHIRAL SYNTHESIS VIA ORGANOBORANES .36. EXCEPTIONALLY ENANTIOSELECTIVE ALLYLBORATIONS OF REPRESENTATIVE HETEROCYCLIC ALDEHYDES AT -100-DEGREES-C UNDER SALT-FREE CONDITIONS [J].
RACHERLA, US ;
LIAO, Y ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6614-6617