TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-CALANOLIDE-A, A NON-NUCLEOSIDE INHIBITOR OF HIV-1 REVERSE-TRANSCRIPTASE

被引:84
作者
CHENERA, B [1 ]
WEST, ML [1 ]
FINKELSTEIN, JA [1 ]
DREYER, GB [1 ]
机构
[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT MED CHEM,POB 1539,KING OF PRUSSIA,PA 19406
关键词
D O I
10.1021/jo00073a015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first syntheses of (+/-)-calanolide A and the related (+/-)-calanolides C and D have been carried out in a short sequence using a Lewis acid-promoted Claisen rearrangement to establish the chromene ring.
引用
收藏
页码:5605 / 5606
页数:2
相关论文
共 43 条
  • [1] THERMAL CYCLIZATION OF SUBSTITUTED ARYL PROPARGYL ETHERS - SCOPE AND REGIOSELECTIVITY OF REACTION IN SYNTHESIS OF SUBSTITUTED 3-CHROMENES
    ANDERSON, WK
    LAVOIE, EJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (22) : 3832 - 3835
  • [2] ATTWOOD MR, 1991, TETRAHEDRON LETT, P811
  • [3] ACID CATALYSIS OF CLAISEN REARRANGEMENT .2. FORMATION OF BENZOFUROBENZOPYRAN AND BENZOFURO[3,2-B]BENZOFURAN SKELETONS FROM 1,4-BIS(ARYLOXY)-2-BUTYNES
    BATES, DK
    JONES, MC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) : 3856 - 3861
  • [4] BLATT AH, 1954, ORG REACTIONS, V1, P342
  • [5] REARRANGEMENT OF ALLYL ARYL ETHERS ALD ALLYL CYCLOHEXADIENONES USING BORON TRICHLORIDE
    BORGULYA, J
    MADEJA, R
    FAHRNI, P
    HANSEN, HJ
    SCHMID, H
    BARNER, R
    [J]. HELVETICA CHIMICA ACTA, 1973, 56 (01) : 14 - 75
  • [6] ANALYSIS OF NONNUCLEOSIDE DRUG-RESISTANT VARIANTS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 REVERSE-TRANSCRIPTASE
    BOYER, PL
    CURRENS, MJ
    MCMAHON, JB
    BOYD, MR
    HUGHES, SH
    [J]. JOURNAL OF VIROLOGY, 1993, 67 (04) : 2412 - 2420
  • [7] STUDIES OF CHROMENES .10. OXIRANES OF NITROCHROMENES
    BROWN, PE
    LEWIS, RA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05): : 573 - 577
  • [8] RELAXANT ACTIVITY OF 4-AMIDO-3,4-DIHYDRO-2H-1-BENZOPYRAN-3-OLS AND 4-AMIDO-2H-1-BENZOPYRANS ON GUINEA-PIG ISOLATED TRACHEALIS
    BUCKLE, DR
    ARCH, JRS
    FENWICK, AE
    HOUGEFRYDRYCH, CSV
    PINTO, IL
    SMITH, DG
    TAYLOR, SG
    TEDDER, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (11) : 3028 - 3034
  • [9] CONVERSION OF PHENOLS INTO CHROMENS - REGIOSPECIFICITY AND SCOPE
    CLARKE, DG
    CROMBIE, L
    WHITING, DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (09): : 1007 - 1015
  • [10] DAHRMARATNE HRW, 1985, PHYTOCHEMISTRY, V24, P1553