A convenient synthesis of a N-protected L-carbamoylpolyoxamic acid derivative:: Total synthesis of (+)-polyoxin J and (+)-polyoxin L

被引:0
|
作者
Uchida, K [1 ]
Kato, K [1 ]
Akita, H [1 ]
机构
[1] Toho Univ, Sch Pharmaceut Sci, Chiba 2748510, Japan
来源
SYNTHESIS-STUTTGART | 1999年 / 09期
关键词
total synthesis; diastereoselective vinylation; polyoxamic acid; polyoxin J; polyoxin L;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient synthesis of the N-protected L-carbamoylpolyoxamic acid derivative 7 from 4-O-tert-butyldiphenylsilyl-2,3-isopropylidene-L-threose (8) using vinylmagnesium bromide and its application to the total syntheses of the peptidyl nucleoside antibiotics, polyoxins J (1) and L (2), are described.
引用
收藏
页码:1678 / 1686
页数:9
相关论文
共 50 条
  • [1] Total syntheses of (-)-polyoxin J and (-)-polyoxin L
    Akita, H
    Uchida, K
    Kato, K
    HETEROCYCLES, 1998, 47 (01) : 157 - 161
  • [2] Total synthesis of (+)-polyoxin J and (+)-polyoxin L (vol 47, pg 157, 1998)
    Akita, H
    Uchida, K
    Kato, K
    HETEROCYCLES, 1999, 51 (05) : 1223 - 1223
  • [3] Total synthesis of (+)-polyoxin J
    Ghosh, AK
    Wang, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08): : 2789 - 2795
  • [4] TOTAL SYNTHESIS OF (+)-POLYOXIN-J
    DONDONI, A
    JUNQUERA, F
    MERCHAN, FL
    MERINO, P
    TEJERO, T
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (20) : 2127 - 2128
  • [6] Applications of sugar nitrones in synthesis: The total synthesis of (+)-polyoxin J
    Dondoni, A
    Franco, S
    Junquera, F
    Merchan, FL
    Merino, P
    Tejero, T
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16): : 5497 - 5507
  • [7] TOTAL SYNTHESIS OF (+)-POLYOXIN-J STARTING FROM MYOINOSITOL
    CHIDA, N
    KOIZUMI, K
    KITADA, Y
    YOKOYAMA, C
    OGAWA, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) : 111 - 113
  • [8] POLYOXIN ANALOGS .3. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF AMINOACYL DERIVATIVES OF POLYOXIN-C AND POLYOXIN-L
    AZUMA, T
    SAITA, T
    ISONO, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1977, 25 (07) : 1740 - 1748
  • [9] SYNTHESES WITH AZIDO SUGARS .9. TOTAL SYNTHESIS OF POLYOXIN J
    KUZUHARA, H
    OHRUI, H
    EMOTO, S
    TETRAHEDRON LETTERS, 1973, (50) : 5055 - 5058
  • [10] CONVENIENT SYNTHESIS OF N-PROTECTED AMINO-ACID AMIDES
    NOZAKI, S
    MURAMATSU, I
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (07) : 2647 - 2648