Preparation of bicyclo[4.3.0]nonanes by an organocatalytic intramolecular Diels-Alder reaction

被引:33
作者
Selkälä, SA [1 ]
Koskinen, AMP [1 ]
机构
[1] Helsinki Univ Technol, Organ Chem Lab, Dept Chem Technol, Helsinki 02015, Finland
关键词
natural products; enantioselectivity; cycloaddition; organocatalysis;
D O I
10.1002/ejoc.200400802
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bicyclo[4.3.0]nonane substructure is an abundant structure found in several natural compounds. A novel enantioselective organocatalytic cycloaddition was used to prepare the bicyclo[4.3.0]nonane skeleton. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码:1620 / 1624
页数:5
相关论文
共 49 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]  
BOECK LD, 1990, Patent No. 375316
[3]   AN EFFICIENT ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-X-14547A (INDANOMYCIN) [J].
BOECKMAN, RK ;
ENHOLM, EJ ;
DEMKO, DM ;
CHARETTE, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4743-4745
[4]   TOTAL SYNTHESIS OF (+/-)-PULOUPONE [J].
BURKE, SD ;
PISCOPIO, AD ;
BUCHANAN, JL .
TETRAHEDRON LETTERS, 1988, 29 (23) :2757-2760
[5]   Studies aimed at the total synthesis of the antitumor antibiotic cochleamycin A. An enantioselective biosynthesis-based pathway to the AB bicyclic core [J].
Chang, JY ;
Paquette, LA .
ORGANIC LETTERS, 2002, 4 (02) :253-256
[6]   Cycloadditions of highly functionalized C-6-synthons to cyclic nitrones [J].
Closa, M ;
deMarch, P ;
Figueredo, M ;
Font, J ;
Soria, A .
TETRAHEDRON, 1997, 53 (49) :16803-16816
[7]   AN INTRIGUING C-16-ALKADIENONE-SUBSTITUTED 2-PYRIDINE FROM A MARINE MOLLUSK [J].
COVAL, SJ ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3024-3025
[8]   Towards the total synthesis of stawamycin. Synthesis of C11-C21 fragment. [J].
Dias, LC ;
Jardim, LSA ;
Ferreira, AA ;
Soarez, HU .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (04) :463-466
[9]   TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC X-14547A (INDANOMYCIN) [J].
EDWARDS, MP ;
LEY, SV ;
LISTER, SG ;
PALMER, BD ;
WILLIAMS, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3503-3516
[10]   AN INTRAMOLECULAR DIELS-ALDER APPROACH TO THE SYNTHESIS OF THE RIGHT HAND HALF OF THE IONOPHORE ANTIBIOTIC X-14547A [J].
EDWARDS, MP ;
LEY, SV ;
LISTER, SG .
TETRAHEDRON LETTERS, 1981, 22 (04) :361-364