SYNTHESIS OF THE C16-C23 EFFECTOR DOMAIN OF FK-506 VIA COPPER-CATALYZED METALATE REARRANGEMENT OF AN ALPHA-ALKOXYALKENYLCUPRATE

被引:0
作者
JAROWICKI, K [1 ]
KOCIENSKI, P [1 ]
NORRIS, S [1 ]
OSHEA, M [1 ]
STOCKS, M [1 ]
机构
[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO17 1BJ,HANTS,ENGLAND
来源
SYNTHESIS-STUTTGART | 1995年 / 02期
关键词
IMMUNOSUPPRESSANT; FK-506; EFFECTOR DOMAIN; 1,2-METALATE REARRANGEMENT; HIGHER ORDER CUPRATE;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 1,2-metallate rearrangement of the putative higher order cuprate 17 derived from reaction of the metallated dihydrofuran 15 with the homocuprate 16 occurred with clean inversion of configuration to give the alkenylcuprate 18. Methylation of 18 followed by Eve simple transformations completed the synthesis of the C16-C23 effector domain of the immunosuppressant FK-506.
引用
收藏
页码:195 / 198
页数:4
相关论文
共 15 条
  • [1] TOTAL SYNTHESES OF CLOSE ANALOGS OF THE IMMUNOSUPPRESSANT FK506
    BATCHELOR, MJ
    GILLESPIE, RJ
    GOLEC, JMC
    HEDGECOCK, CJR
    JONES, SD
    MURDOCH, R
    [J]. TETRAHEDRON, 1994, 50 (03) : 809 - 826
  • [2] BELSHAW PJ, 1994, SYNLETT, P381
  • [3] OBSERVATION OF ALPHA-SILYL CARBANIONS IN THE METALATION OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
    FRIESEN, RW
    STURINO, CF
    DALJEET, AK
    KOLACZEWSKA, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1944 - 1947
  • [4] A FACILE GENERATION OF ALPHA-SILYL CARBANIONS
    IMANIEH, H
    QUAYLE, P
    VOADEN, M
    STREET, SDA
    [J]. TETRAHEDRON LETTERS, 1992, 33 (04) : 543 - 546
  • [5] SYNTHESIS OF THE 9,10-ACETONIDE OF 9-DIHYDRO-FK-506
    IRELAND, RE
    HIGHSMITH, TK
    GEGNAS, LD
    GLEASON, JL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) : 5071 - 5073
  • [6] CHEMISTRY OF TRICARBONYL HEMIKETALS AND APPLICATION OF EVANS TECHNOLOGY TO THE TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506
    JONES, TK
    REAMER, RA
    DESMOND, R
    MILLS, SG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) : 2998 - 3017
  • [7] KOCIENSKI P, 1990, TETRAHEDRON LETT, V31, P1637
  • [8] CONVENIENT ACCESS TO 2 ENANTIOMERIC OXIRANE SYNTHONS BEARING A QUATERNARY GEM-DIMETHYL CARBON CENTER - SYNTHESIS OF 3S-(+) AND 3R-(-)-2,2-DIMETHYL-3,4-OXO-1-BUTANOL FROM R-(-)-PANTOLACTONE
    LAVALLEE, P
    RUEL, R
    GRENIER, L
    BISSONNETTE, M
    [J]. TETRAHEDRON LETTERS, 1986, 27 (06) : 679 - 682
  • [9] TOTAL SYNTHESIS OF FK506 AND AN FKBP PROBE REAGENT, (C8,C9-(C-13)2)-FK506
    NAKATSUKA, M
    RAGAN, JA
    SAMMAKIA, T
    SMITH, DB
    UEHLING, DE
    SCHREIBER, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) : 5583 - 5601
  • [10] MOLECULAR RECOGNITION OF IMMUNOPHILINS AND IMMUNOPHILIN-LIGAND COMPLEXES
    SCHREIBER, SL
    LIU, J
    ALBERS, MW
    ROSEN, MK
    STANDAERT, RF
    WANDLESS, TJ
    SOMERS, PK
    [J]. TETRAHEDRON, 1992, 48 (13) : 2545 - 2558