Total synthesis of bastadins 2, 3, and 6

被引:29
作者
Guo, ZW [1 ]
Machiya, K [1 ]
Salamonczyk, GM [1 ]
Sih, CJ [1 ]
机构
[1] Univ Wisconsin, Sch Pharm, Madison, WI 53706 USA
关键词
D O I
10.1021/jo9721204
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.
引用
收藏
页码:4269 / 4276
页数:8
相关论文
共 23 条
  • [1] THE BASTADINS REVISITED - NEW CHEMISTRY FROM THE AUSTRALIAN MARINE SPONGE IANTHELLA-BASTA
    BUTLER, MS
    LIM, TK
    CAPON, RJ
    HAMMOND, LS
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (02) : 287 - 296
  • [2] A NEW BASTADIN FROM THE SPONGE PSAMMAPLYSILLA-PURPUREA
    CARNEY, JR
    SCHEUER, PJ
    KELLYBORGES, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01): : 153 - 157
  • [3] PH-DEPENDENCE OF THE ACTIVE-SITE OF HORSERADISH-PEROXIDASE COMPOUND-II
    CHANG, CS
    YAMAZAKI, I
    SINCLAIR, R
    KHALID, S
    POWERS, L
    [J]. BIOCHEMISTRY, 1993, 32 (03) : 923 - 928
  • [4] ISOLATION OF A NOVEL BASTADIN FROM THE TEMPERATE MARINE SPONGE IANTHELLA SP
    DEXTER, AF
    GARSON, MJ
    HEMLING, ME
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (05): : 782 - 786
  • [5] INTRAMOLECULAR CYCLIZATION OF PHENOLIC OXIMES .1. CYCLIZATIONS WITH MANGANESE(III) TRIS(ACETYLACETONATE)
    FORRESTER, AR
    THOMSON, RH
    WOO, SO
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22): : 2340 - 2348
  • [6] FRQNKLIN MA, 1996, J NAT PRODUCTS, V59, P1121
  • [7] ISOLATION AND STRUCTURE ELUCIDATION OF 34-SULFATOBASTADIN-13, AN INHIBITOR OF THE ENDOTHELIN A RECEPTOR, FROM A MARINE SPONGE OF THE GENUS IANTHELLA
    GULAVITA, NK
    WRIGHT, AE
    MCCARTHY, PJ
    POMPONI, SA
    KELLYBORGES, M
    CHIN, M
    SILLS, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (09): : 1613 - 1617
  • [8] Enzymatic oxidative phenolic coupling
    Guo, ZW
    Salamonczyk, GM
    Han, K
    Machiya, K
    Sih, CJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 6700 - 6701
  • [9] KAZLAUSKAS R, 1981, AUST J CHEM, V34, P765, DOI 10.1071/CH9810765
  • [10] MACK MM, 1994, J BIOL CHEM, V269, P23236