EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .26. THE PREPARATION OF CHIRAL INTERMEDIATES FOR ANTHRACYCLINONE SYNTHESIS

被引:5
|
作者
BEAUREGARD, DA [1 ]
CAMBIE, RC [1 ]
DANSTED, PC [1 ]
RUTLEDGE, PS [1 ]
WOODGATE, PD [1 ]
机构
[1] UNIV AUCKLAND,DEPT CHEM,AUCKLAND,NEW ZEALAND
关键词
D O I
10.1071/CH9950669
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(2'R)-1,5-Dimethoxy-2(2'-methyloxiran-2'-y (8), an intermediate for the synthesis of fridamycin E, has been prepared enantioselectively via the diol (15). The diol (15) was prepared in high yield by asymmetric cis-hydroxylation of the alkene (11). The analogous diol (22), a vineomycinone B-2 precursor, was also prepared.
引用
收藏
页码:669 / 676
页数:8
相关论文
共 50 条
  • [21] Experiments directed towards the synthesis of anthracyclinones .31. Reductive Claisen rearrangements of bis(allyloxy)anthraquinones
    HarringtonFrost, NM
    Milbank, JBJ
    Rutledge, PS
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (04) : 379 - 389
  • [22] EXPERIMENTS DIRECTED TOWARDS SYNTHESIS OF ANTHRACYCLINONES .3. BETA-FORMYLATION OF HYDROXYANTHRAQUINONES BY CLAISEN REARRANGEMENT
    ROBERTS, JL
    RUTLEDGE, PS
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (08) : 1743 - 1746
  • [23] SYNTHESIS OF HETEROCYCLIC INTERMEDIATES RELATED TO ANTHRACYCLINONES
    HARPER, MF
    MORLEY, JO
    PRESTON, PN
    JOURNAL OF CHEMICAL RESEARCH-S, 1985, (11): : 338 - 339
  • [24] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .17. CYCLIZATION REACTIONS OF SOME ANTHRAQUINONE CONDURITOL ACETALS
    CAMBIE, RC
    HOLROYD, SE
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (01) : 37 - 47
  • [25] Experiments directed towards the synthesis of anthracyclinones. XXI. Claisen rearrangements of some mixed allyl ethers
    Beauregard, Daniel A.
    Cambie, Richard C.
    Higgs, Kerianne C.
    Rutledge, Peter S.
    Woodgate, Paul D.
    Australian Journal of Chemistry, 1994, 47 (07)
  • [26] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .19. ELABORATION OF 2-FORMYLQUINIZARIN THROUGH A WITTIG REACTION
    BONIFACE, PJ
    CAMBIE, RC
    CARROLL, DR
    MARSH, NF
    MILBANK, JBJ
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (03) : 441 - 449
  • [27] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .15. NOVEL SYNTHETIC HOMOCHIRAL CHLOROANTHRACYCLINES FROM ACETAL CYCLIZATION
    BROWN, EG
    CAMBIE, RC
    HOLROYD, SE
    JOHNSON, M
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (06) : 1019 - 1034
  • [28] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .25. SYNTHESIS OF A VINEOMYCINONE B-2 METHYL-ESTER INTERMEDIATE FROM ANTHRARUFIN
    BERCICH, MD
    CAMBIE, RC
    HOWE, TA
    RUTLEDGE, PS
    THOMSON, SD
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (03) : 531 - 549
  • [29] APPROACH TO VERSATILE INTERMEDIATES IN THE SYNTHESIS OF ANTHRACYCLINONE AGLYCONE ANALOGS
    OCONNOR, U
    ROSEN, W
    TETRAHEDRON LETTERS, 1979, (07) : 601 - 604
  • [30] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .11. A NEW DIELS-ALDER ENTRY TO (+/-)-4-DEMETHOXYDAUNOMYCINONE
    BODDY, IK
    CAMBIE, RC
    MARSH, NF
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (05) : 821 - 825