A SHORT, DIASTEREOSPECIFIC APPROACH TO SYMMETRICAL AND UNSYMMETRICAL 2,6-DIARYL-3,7-DIOXABICYCLO[3.3.0]OCTANE LIGNANS

被引:21
作者
BRADLEY, HM [1 ]
KNIGHT, DW [1 ]
机构
[1] CHEM DEPT,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1039/c39910001641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enolate Claisen rearrangement of the lactone 7 leads to the tetrahydrofuran (THF) ester 9 as a single diastereoisomer, reduction of which gives the general bis-THF lignan precursor 2.
引用
收藏
页码:1641 / 1643
页数:3
相关论文
共 16 条
[1]   AN APPROACH TO CHIRAL TRISUBSTITUTED PYRROLIDINES BY ENOLATE CLAISEN REARRANGEMENT OF AZALACTONES DERIVED FROM ALPHA-AMINO-ACIDS [J].
COOPER, J ;
KNIGHT, DW ;
GALLAGHER, PT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (04) :705-713
[2]  
DAUZONNE D, 1987, SYNTHESIS-STUTTGART, P399
[3]   BETA-CYANO- AND BETA-CARBETHOXY SULFIDES SULFOXIDE AND SULFONES AND THEIR KNOEVENAGEL CONDENSATION [J].
DRESSLER, H ;
GRAHAM, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :985-&
[4]   ACIDIC TRANSFORMATION OF SESAMOLIN, THE SESAME-OIL CONSTITUENT, INTO AN ANTIOXIDANT BISEPOXYLIGNAN, SESAMINOL [J].
FUKUDA, Y ;
ISOBE, M ;
NAGATA, M ;
OSAWA, T ;
NAMIKI, M .
HETEROCYCLES, 1986, 24 (04) :923-926
[5]   CLAISEN-REARRANGEMENT-MEDIATED RING CONTRACTION OF MACROCYCLIC LACTONES - A NEW APPROACH TO CARBOCYCLES AND HETEROCYCLES [J].
FUNK, RL ;
ABELMAN, MM ;
MUNGER, JD .
TETRAHEDRON, 1986, 42 (11) :2831-2846
[6]   THE CONSTITUENTS OF NATURAL PHENOLIC RESINS .23. THE CONSTITUTION OF SESAMOLIN [J].
HASLAM, E ;
HAWORTH, RD .
JOURNAL OF THE CHEMICAL SOCIETY, 1955, :827-833
[8]   SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ACETALIC LIGNAN (+)-PHRYMAROLIN-I [J].
ISHIBASHI, F ;
TANIGUCHI, E .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (12) :4361-4366
[9]   A TOTAL SYNTHESIS OF RACEMIC PAULOWNIN USING A TYPE-II PHOTOCYCLIZATION REACTION [J].
KRAUS, GA ;
CHEN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3464-3466
[10]   FACILE SYNTHESIS OF LACTONES [J].
MUKAIYAMA, T ;
USUI, M ;
SAIGO, K .
CHEMISTRY LETTERS, 1976, (01) :49-50