TOTAL SYNTHESIS OF (+)-LACTACYSTIN FROM D-GLUCOSE

被引:85
作者
CHIDA, N
TAKEOKA, J
TSUTSUMI, N
OGAWA, S
机构
关键词
D O I
10.1039/c39950000793
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the gamma-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
引用
收藏
页码:793 / 794
页数:2
相关论文
共 20 条
  • [1] ASYMMETRIC ALPHA-AMINO-ACID SYNTHESIS USING [3.3] REARRANGEMENT OF ALLYLIC TRIFLUOROACETIMIDATES - SYNTHESIS OF THYMINE POLYOXIN-C
    CHEN, A
    SAVAGE, I
    THOMAS, EJ
    WILSON, PD
    [J]. TETRAHEDRON LETTERS, 1993, 34 (42) : 6769 - 6772
  • [2] TOTAL SYNTHESIS OF LACTACYSTIN
    COREY, EJ
    REICHARD, GA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10677 - 10678
  • [3] STUDIES ON THE TOTAL SYNTHESIS OF LACTACYSTIN - AN IMPROVED ALDOL COUPLING REACTION AND A BETA-LACTONE INTERMEDIATE IN THIOL ESTER FORMATION
    COREY, EJ
    REICHARD, GA
    KANIA, R
    [J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 6977 - 6980
  • [4] SYNTHESIS OF (6R,7S)-LACTACYSTIN AND 6-DEOXYLACTACYSTIN FROM A COMMON INTERMEDIATE
    COREY, EJ
    REICHARD, GA
    [J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 6973 - 6976
  • [5] AN ENANTIOSELECTIVE SYNTHESIS OF (6R)-LACTACYSTIN
    COREY, EJ
    CHOI, SY
    [J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 6969 - 6972
  • [6] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES
    DAVID, S
    HANESSIAN, S
    [J]. TETRAHEDRON, 1985, 41 (04) : 643 - 663
  • [7] A BETA-LACTONE RELATED TO LACTACYSTIN INDUCES NEURITE OUTGROWTH IN A NEUROBLASTOMA CELL-LINE AND INHIBITS CELL-CYCLE PROGRESSION IN AN OSTEOSARCOMA CELL-LINE
    FENTEANY, G
    STANDAERT, RF
    REICHARD, GA
    COREY, EJ
    SCHREIBER, SL
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (08) : 3358 - 3362
  • [8] BIOSYNTHESIS OF LACTACYSTIN - ORIGIN OF THE CARBONS AND STEREOSPECIFIC NMR ASSIGNMENT OF THE 2 DIASTEREOTOPIC METHYL-GROUPS
    NAKAGAWA, A
    TAKAHASHI, S
    UCHIDA, K
    MATSUZAKI, K
    OMURA, S
    NAKAMURA, A
    KURIHARA, N
    NAKAMATSU, T
    MIYAKE, Y
    TAKE, K
    KAINOSHO, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (28) : 5009 - 5012
  • [9] STRUCTURE OF LACTACYSTIN, A NEW MICROBIAL METABOLITE WHICH INDUCES DIFFERENTIATION OF NEUROBLASTOMA-CELLS
    OMURA, S
    MATSUZAKI, K
    FUJIMOTO, T
    KOSUGE, K
    FURUYA, T
    FUJITA, S
    NAKAGAWA, A
    [J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (01) : 117 - 118
  • [10] LACTACYSTIN, A NOVEL MICROBIAL METABOLITE, INDUCES NEURITOGENESIS OF NEUROBLASTOMA-CELLS
    OMURA, S
    FUJIMOTO, T
    OTOGURO, K
    MATSUZAKI, K
    MORIGUCHI, R
    TANAKA, H
    SASAKI, Y
    [J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (01) : 113 - 116