SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN

被引：18

作者：

SAITO, S ^{[1
]}

TAMURA, O ^{[1
]}

KOBAYASHI, Y ^{[1
]}

MATSUDA, F ^{[1
]}

KATOH, T ^{[1
]}

TERASHIMA, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 21期

关键词：

ASYMMETRIC SYNTHESIS; QUINOCARCIN; ANTITUMOR ANTIBIOTIC; ABE RING SYSTEM; DIASTEREOSELECTIVE REDUCTION; 4-O-BENZYL-2,3-O-ISOPROPYLIDENETHREOSE;

D O I：

10.1016/S0040-4020(01)80641-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomeric pairs of the ABE ring system (5 and ent-5) and its analogues (6, ent-6, 7, and ent-7) of quinocarcin (1), a prominent antitumor antibiotic, were synthesized in >95% ee with an aim to elucidate structure-activity relationships of 1. The key step of the synthesis includes novel diastereoselective reduction of 3,4-dihydroisoquinoline derivatives 25 and ent-25, wherein each enantiomer of 4-O-benzyl-2,3-O-isopropylidene-threose (I and ent-I) is employed as a chiral auxiliary.

引用

页码：6193 / 6208

页数：16

共 8 条

[1] SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .2. SYNTHESIS OF AN ENANTIOMERIC PAIR OF THE ABC RING-SYSTEM OF QUINOCARCIN
SAITO, S
TANAKA, K
NAKATANI, K
MATSUDA, F
KATOH, T
TERASHIMA, S
TETRAHEDRON, 1994, 50 (21) : 6209 - 6220
[2] SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .4. TOTAL SYNTHESIS OF ENANTIOMERIC PAIRS OF QUINOCARCIN AND 10-DECARBOXYQUINOCARCIN
KATOH, T
KIRIHARA, M
NAGATA, Y
KOBAYASHI, Y
ARAI, K
MINAMI, J
TERASHIMA, S
TETRAHEDRON, 1994, 50 (21) : 6239 - 6258
[3] SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .5. SYNTHESIS AND ANTITUMOR-ACTIVITY OF VARIOUS STRUCTURAL TYPES OF QUINOCARCIN CONGENERS
KATOH, T
KIRIHARA, M
YOSHINO, T
TAMURA, O
IKEUCHI, F
NAKATANI, K
MATSUDA, F
YAMADA, K
GOMI, K
ASHIZAWA, T
TERASHIMA, S
TETRAHEDRON, 1994, 50 (21) : 6259 - 6270
[4] SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .3. SYNTHESIS OF 5-SUBSTITUTED AND 3,5-DISUBSTITUTED-2-FORMYL-PYRROLIDINE DERIVATIVES, THE KEY D-RING FRAGMENTS OF ENANTIOMERIC PAIRS OF QUINOCARCIN AND 10-DECARBOXYQUINOCARCIN
KATOH, T
NAGATA, Y
KOBAYASHI, Y
ARAI, K
MINAMI, J
TERASHIMA, S
TETRAHEDRON, 1994, 50 (21) : 6221 - 6238
[5] Studies on the asymmetric synthesis of pyrrolidine alkaloids and related compounds .1. Synthesis of a chiral precursor for preussin and AHPPA
Huang, PQ
Ruan, YP
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1995, 16 (12): : 1914 - 1916
[6] SYNTHETIC STUDIES ON DUOCARMYCIN .1. TOTAL SYNTHESIS OF DL-DUOCARMYCIN-A AND ITS 2-EPIMER
FUKUDA, Y
ITOH, Y
NAKATANI, K
TERASHIMA, S
TETRAHEDRON, 1994, 50 (09) : 2793 - 2808
[7] Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin
Hashimoto, M
Matsumoto, M
Terashima, S
TETRAHEDRON, 2003, 59 (17) : 3019 - 3040
[8] Synthetic studies of himbacine, a potent antagonist of the muscarinic M2 subtype receptor 1.: Stereoselective total synthesis and antagonistic activity of enantiomeric pairs of himbacine and (2′S,6′R)-diepihimbacine, 4-epihimbacine, and novel himbacine congeners
Takadoi, M
Katoh, T
Ishiwata, A
Terashima, S
TETRAHEDRON, 2002, 58 (50) : 9903 - 9923

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