SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .2. SYNTHESIS OF AN ENANTIOMERIC PAIR OF THE ABC RING-SYSTEM OF QUINOCARCIN

被引：15

作者：

SAITO, S ^{[1
]}

TANAKA, K ^{[1
]}

NAKATANI, K ^{[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; ABC RING SYSTEM; DIASTEREOSELECTIVE REDUCTION; INTRAMOLECULAR N; O-ACETAL FORMATION;

D O I：

10.1016/S0040-4020(01)80642-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiomeric pair of the ABC ring system (5 and ent-5) of quinocarcin (1), a patent antitumor antibiotic, was synthesized in >95% ee with an. aim to disclose novel aspects of the structure-activity relationships of 1. The key features of the synthesis consist of novel diastereoselective reduction of 1,3-disubstituted isoquinoline derivatives 29 and ent-29 to control stereochemistries at the C6 and C11a positions in 5 and ent-5 simultaneously in a single step and intramolecular N,O-acetal formation of amino aldehydes 6 and ent-6 to complete the requisite skeletal framework.

引用

页码：6209 / 6220

页数：12

共 50 条

[1] SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN
SAITO, S
TAMURA, O
KOBAYASHI, Y
MATSUDA, F
KATOH, T
TERASHIMA, S
TETRAHEDRON, 1994, 50 (21) : 6193 - 6208
[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] CHIRAL SYNTHESIS OF THE ABC-RING SYSTEM OF QUINOCARCIN
SAITO, S
TANAKA, K
NAKATANI, K
MATSUDA, F
TERASHIMA, S
TETRAHEDRON LETTERS, 1989, 30 (52) : 7423 - 7426
[5] 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
[6] Synthesis and cytotoxicity of natural (-)-quinocarcin and its related compounds
Pure Appl Chem, 3 (703):
[7] Synthesis and cytotoxicity of natural (-)-quinocarcin and its related compounds
Katoh, T
Terashima, S
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) : 703 - 706
[8] SYNTHETIC STUDIES TOWARD VERRUCAROL .2. SYNTHESIS OF THE AB RING-SYSTEM
KRAUS, GA
ROTH, B
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24): : 4825 - 4830
[9] SYNTHETIC STUDIES ON CYATHINS - SYNTHESIS OF THE RING-SYSTEM
WARD, DE
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (10): : 2380 - 2384
[10] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .45. A NEW HETEROCYCLIC RING-SYSTEM
KARDOSBALOGH, Z
SOTI, F
INCZE, M
KAJTARPEREDY, M
SZANTAY, C
HETEROCYCLES, 1989, 29 (08) : 1589 - 1593

← 1 2 3 4 5 →