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

被引：85

作者：

CHIDA, N

TAKEOKA, J

TSUTSUMI, N

OGAWA, S

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 07期

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

页码：793 / 794

页数：2

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

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