STEREOSELECTIVE SYNTHESIS OF (+/-)-1-O-METHYLLOGANIN, 10-HYDROXYLOGANIN, SECOLOGANIN, AND SWEROSIDE AGLUCONS FROM A COMMON 1-HYDROXY-4A,5,8,8A-TETRAHYDROISOCHROMENE SYNTHON

被引:16
作者
NAKANE, M [1 ]
HUTCHINSON, CR [1 ]
机构
[1] UNIV WISCONSIN,SCH PHARM,MADISON,WI 53706
关键词
D O I
10.1021/jo01309a037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
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页码:4233 / 4236
页数:4
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共 15 条
  • [1] AUYEUNG BW, 1977, J CHEM SOC CHEM COMM, P81
  • [2] ALKALOID BIOSYNTHESIS .15. PARTIAL SYNTHESIS AND ISOLATION OF VINCOSIDE AND ISOVINCOSIDE - BIOSYNTHESIS OF 3 MAJOR CLASSES OF INDOLE ALKALOIDS FROM VINCOSIDE
    BATTERSB.AR
    BURNETT, AR
    PARSONS, PG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (08): : 1193 - &
  • [3] ALKALOID BIOSYNTHESIS .14. SECOLOGANIN - ITS CONVERSION INTO IPECOSIDE AND ITS ROLE AS BIOLOGICAL PRECURSOR OF INDOLE ALKALOIDS
    BATTERSBY, AR
    BURNETT, AR
    PARSONS, PG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (08): : 1187 - +
  • [4] BRIGGS LH, 1963, TETRAHEDRON LETT, P69
  • [5] BUCHI G, 1967, J AM CHEM SOC, V89, P2776
  • [6] BUCHI G, 1973, J AM CHEM SOC, V95, P540
  • [7] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION
    HOUSE, HO
    CRUMRINE, DS
    TERANISH.AY
    OLMSTEAD, HD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3310 - 3324
  • [8] EFFICIENT STEREOSELECTIVE SYNTHESIS OF (+/-)-SWEROSIDE AND (+/-)-SECOLOGANIN AGLUCONE O-METHYL ETHERS
    HUTCHINSON, CR
    MATTES, KC
    NAKANE, M
    PARTRIDGE, JJ
    USKOKOVIC, MR
    [J]. HELVETICA CHIMICA ACTA, 1978, 61 (04) : 1221 - 1225
  • [9] IRIDOIDS .5. BIOGENETIC TYPE SYNTHESIS OF SECOLOGANIN-AND SWEROSIDE AGLYCONE O-METHYL ETHER
    KINAST, G
    TIETZE, LF
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (11): : 3626 - 3639
  • [10] STEREO-SELECTION IN ALDOL CONDENSATION
    KLESCHICK, WA
    BUSE, CT
    HEATHCOCK, CH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (01) : 247 - 248