An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

被引：62
作者：
Gallos, JK [1 ]
Stathakis, CI [1 ]
Kotoulas, SS [1 ]
Koumbis, AE [1 ]
机构：
[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 17期
关键词：
D O I：
10.1021/jo050987t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.
引用
收藏
页码：6884 / 6890
页数：7
相关论文
共 102 条
  • [41] Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid
    Jiang, SD
    McCullough, KJ
    Mekki, B
    Singh, G
    Wightman, RH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1805 - 1814
  • [42] ENANTIOSPECIFIC SYNTHESIS OF (-)-5-EPI-SHIKIMIC ACID AND A NEW ROUTE TO (-)-SHIKIMIC ACID
    JIANG, SD
    MEKKI, B
    SINGH, G
    WIGHTMAN, RH
    [J]. TETRAHEDRON LETTERS, 1994, 35 (30) : 5505 - 5508
  • [43] Practical synthesis of D- and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus)
    Jin, YH
    Liu, P
    Wang, JN
    Baker, R
    Huggins, J
    Chu, CK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) : 9012 - 9018
  • [44] SYNTHESIS OF PGE1 AND VARIOUS 10-ALPHA-HYDROXYPROSTAGLANDINS
    JOHNSON, CR
    CHEN, YF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) : 3352 - 3357
  • [45] DEVELOPMENT OF A TRIPLY CONVERGENT ALDOL APPROACH TO PROSTANOIDS
    JOHNSON, CR
    CHEN, YF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) : 3344 - 3351
  • [46] CHEMOENZYMATIC SYNTHESIS OF 1,3-DIDEOXYNOJIRIMYCIN
    JOHNSON, CR
    GOLEBIOWSKI, A
    BRAUN, MP
    SUNDRAM, H
    [J]. TETRAHEDRON LETTERS, 1994, 35 (12) : 1833 - 1834
  • [47] JOHNSON CR, 1995, SYNLETT, P313
  • [48] CHEMOENZYMATIC SYNTHESIS OF TRANS-4,5-DIHYDROXYCYCLOPENT-2-ENONES - CONVERSION TO D-1-DEOXYNOJIRIMYCIN
    JOHNSON, CR
    NERURKAR, BM
    GOLEBIOWSKI, A
    SUNDRAM, H
    ESKER, JL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) : 1139 - 1140
  • [49] A 2-STEP, 3-COMPONENT SYNTHESIS OF PGE(1) - UTILIZATION OF ALPHA-IODOENONES IN PD(0)-CATALYZED CROSS-COUPLINGS OF ORGANOBORANES
    JOHNSON, CR
    BRAUN, MP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) : 11014 - 11015
  • [50] DIRECT ALPHA-IODINATION OF CYCLOALKENONES
    JOHNSON, CR
    ADAMS, JP
    BRAUN, MP
    SENANAYAKE, CBW
    WOVKULICH, PM
    USKOKOVIC, MR
    [J]. TETRAHEDRON LETTERS, 1992, 33 (07) : 917 - 918
12345678910