Total Synthesis of Penostatin B

被引:34
作者
Fujioka, Kosuke [1 ]
Yokoe, Hiromasa [1 ]
Yoshida, Masahiro [1 ]
Shishido, Kozo [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
关键词
ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CYTOTOXIC METABOLITES; CYCLIZATIONS; LACTONES; FRAGMENT; STRATEGY; HYDRIDE;
D O I
10.1021/ol203021c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of penostatin B has been accomplished by using a highly diastereoselective Pauson-Khand reaction and an efficient relay ring-closing metathesis for the construction of the basic carbon skeleton of the natural product as the key steps.
引用
收藏
页码:244 / 247
页数:4
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共 30 条
  • [1] Synthesis of a promising immunosuppressant: FR252921
    Amans, Dominique
    Bellosta, Veronique
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2007, 9 (23) : 4761 - 4764
  • [2] PROMOTERS FOR THE (ALKYNE)HEXACARBONYLDICOBALT-BASED CYCLOPENTENONE SYNTHESIS
    CHUNG, YK
    LEE, BY
    JEONG, N
    HUDECEK, M
    PAUSON, PL
    [J]. ORGANOMETALLICS, 1993, 12 (01) : 220 - 223
  • [3] A short synthesis of the C1-C7 fragment of methymycin by ring-closing olefin metathesis
    Cossy, J
    Bauer, D
    Bellosta, V
    [J]. TETRAHEDRON LETTERS, 1999, 40 (22) : 4187 - 4188
  • [4] A convergent approach toward phoslactomycins and leustroducsins
    Druais, Valerie
    Hall, Michael J.
    Corsi, Camilla
    Wendeborn, Sebastian V.
    Meyer, Christophe
    Cossy, Janine
    [J]. TETRAHEDRON, 2010, 66 (33) : 6358 - 6375
  • [5] Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity
    Fukuda, Koichiro
    Miyashita, Masaaki
    Tanino, Keiji
    [J]. TETRAHEDRON LETTERS, 2010, 51 (34) : 4523 - 4525
  • [6] Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations
    Furstner, A
    Langemann, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) : 9130 - 9136
  • [7] Ring-closing metathesis strategy to unsaturated γ- and δ-lactones:: Synthesis of hydroxyethylene isostere for protease inhibitors
    Ghosh, AK
    Cappiello, J
    Shin, D
    [J]. TETRAHEDRON LETTERS, 1998, 39 (26) : 4651 - 4654
  • [8] Total Synthesis of (-)-Callipeltoside A
    Hoye, Thomas R.
    Danielson, Michael E.
    May, Aaron E.
    Zhao, Hongyu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) : 7052 - 7060
  • [9] Relay ring-closing metathesis (RRCM): A strategy for directing metal movement throughout olefin metathesis sequences
    Hoye, TR
    Jeffrey, CS
    Tennakoon, MA
    Wang, JZ
    Zhao, HY
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) : 10210 - 10211
  • [10] DICOBALTOCTACARBONYL-MEDIATED CYCLIZATIONS OF ELECTRON-DEFICIENT ALKYNONES
    HOYE, TR
    SURIANO, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1659 - 1660