Stereoselective Synthesis of Substituted 3a-Hydroxy Diquinanones and 3a-Hydroxy Hydrindanones via Intramolecular Cycloaddition of Nitrile Oxides

被引:2
作者
Chapelon, Anne-Sophie [1 ]
Giorgi, Michel [2 ]
Ollivier, Cyril [1 ]
Santelli, Maurice [1 ]
机构
[1] CNRS 6263, Synth Organ Lab, Equipe Chirosci, Marseille, France
[2] Univ Aix Marseille, Fac Sci St Jerome, Marseille, France
关键词
Diquinanones; hydrindanones; intramolecular cyloaddition; nitrile oxides; STEREOCONTROLLED TOTAL-SYNTHESIS; FORMAL TOTAL SYNTHESIS; BETA-HYDROXY KETONES; 1,3-DIPOLAR CYCLOADDITIONS; DIPOLAR CYCLOADDITIONS; NATURAL-PRODUCTS; EPOTHILONE-A; INOC ROUTE; RING; DERIVATIVES;
D O I
10.1080/00397910902948273
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
trans-1,3-Divinylcyclopentanes bearing a -nitroalkyl chain (C2 or C3) in the 2-position were submitted to an intramolecular nitrile oxide cycloaddition process to give tricyclic isoxazoline precursors of 4-hydroxymethylbicyclo[3.3.0]octan-1-ol-3-ones or 5-hydroxymethyl-9-vinylbicyclo[4.3.0]nonan-1-ol-4-ones.
引用
收藏
页码:87 / 103
页数:17
相关论文
共 85 条
[1]   Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides [J].
Alcaide, B ;
Almendros, P ;
Sáez, E .
ARKIVOC, 2004, :137-152
[2]  
ANDERSON GD, 1972, TETRAHEDRON LETT, P4423
[3]   STEREOSELECTIVITY OF INTRAMOLECULAR NITRILE OXIDE CYCLOADDITIONS TO Z-CHIRAL ALKENE AND E-CHIRAL ALKENE [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
GENNARI, C ;
RAIMONDI, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4674-4681
[4]   Total synthesis of the sesquiterpene (±)-illudin C via an intramolecular nitrile oxide cycloaddition [J].
Aungst, RA ;
Chan, C ;
Funk, RL .
ORGANIC LETTERS, 2001, 3 (16) :2611-2613
[5]   SYNTHETIC STUDIES TOWARDS FORSKOLIN [J].
BARALDI, PG ;
BARCO, A ;
BENETTI, S ;
FERRETTI, V ;
POLLINI, GP ;
POLO, E ;
ZANIRATO, V .
TETRAHEDRON, 1989, 45 (05) :1517-1532
[6]   THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION ROUTE TO FORSKOLIN [J].
BARALDI, PG ;
BARCO, A ;
BENETTI, S ;
POLLINI, GP ;
POLO, E ;
SIMONI, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :757-758
[7]  
BARALDI PG, 1987, SYNTHESIS-STUTTGART, P276
[8]  
BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857
[9]   A [3+2]-NITRILE OXIDE CYCLOADDITION APPROACH TO (-)-PYRENOPHORIN, AND ROSEFURAN [J].
BARCO, A ;
BENETTI, S ;
DERISI, C ;
POLLINI, GP ;
ZANIRATO, V .
TETRAHEDRON, 1995, 51 (28) :7721-7726
[10]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585