Total Synthesis and Determination of the Absolute Configuration of (-)-Idesolide

被引:22
作者
Yamakoshi, Hiroyuki [1 ]
Shibuya, Masatoshi [1 ]
Tomizawa, Masaki [1 ]
Osada, Yuji [1 ]
Kanoh, Naoki [1 ]
Iwabuchi, Yoshiharu [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
关键词
ALKALOIDS; ALCOHOLS; DIMER;
D O I
10.1021/ol9029676
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)-4-Bn-1-Bu-AZADOH- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide is determined to be 2R,2'S,3aS,7aR.
引用
收藏
页码:980 / 983
页数:4
相关论文
共 30 条
  • [1] STRUCTURE OF MANASSES DIMER FROM ENDO-2-HYDROXYEPICAMPHOR BY NOE DIFFERENCE SPECTROSCOPY
    BANKS, MR
    GOSNEY, I
    GRANT, KJ
    REED, D
    [J]. MAGNETIC RESONANCE IN CHEMISTRY, 1992, 30 (10) : 996 - 999
  • [2] REARRANGEMENTS OF ALPHA-HYDROXY KETALS AND DERIVATIVES OF ALPHA-HYDROXY KETALS
    CREARY, X
    ROLLIN, AJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) : 4231 - 4238
  • [3] REACTION OF ALPHA-KETO TRIFLATES WITH SODIUM METHOXIDE
    CREARY, X
    ROLLIN, AJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) : 4226 - 4230
  • [4] Trichloroisocyanuric/TEMPO oxidation of alcohols under mild conditions: A close investigation
    De Luca, L
    Giacomelli, G
    Masala, S
    Porcheddu, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) : 4999 - 5001
  • [5] A PHYTOCHEMICAL INVESTIGATION OF HOMALIUM-CEYLANICUM
    EKABO, OA
    FARNSWORTH, NR
    SANTISUK, T
    REUTRAKUL, V
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (05): : 699 - 707
  • [6] STRUCTURE OF THE DIMER OF RACEMIC EXO-3-HYDROXY-BICYCLO[2.2.1]HEPTAN-2-ONE
    JAUCH, J
    SCHURIG, V
    WALZ, L
    [J]. ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1991, 196 (1-4): : 255 - 260
  • [7] 4-(tert-butyldimethylsilyloxy)benzylidene acetal:: a novel benzylidene-type protecting group for 1,2-diols
    Kaburagi, Y
    Osajima, H
    Shimada, K
    Tokuyama, H
    Fukuyama, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (19) : 3817 - 3821
  • [8] Inhibitory activity of phenolic glycosides from the fruits of Idesia polycarpa on lipopolysaccha ride-induced nitric oxide production in BV2 microglia
    Kim, Seung Hyun
    Jang, Young Pyo
    Sung, Sang Hyun
    Kim, Young Choong
    [J]. PLANTA MEDICA, 2007, 73 (02) : 167 - 169
  • [9] Idesolide:: A new spiro compound from Idesia polycarpa
    Kim, SH
    Sung, SH
    Choi, SY
    Chung, YK
    Kim, J
    Kim, YC
    [J]. ORGANIC LETTERS, 2005, 7 (15) : 3275 - 3277
  • [10] KINOSHITA S, 2003, ELECTROCHIM ACTA, V48, P1589