SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .4. TOTAL SYNTHESIS OF ENANTIOMERIC PAIRS OF QUINOCARCIN AND 10-DECARBOXYQUINOCARCIN

被引：36

作者：

KATOH, T ^{[1
]}

KIRIHARA, M ^{[1
]}

NAGATA, Y ^{[1
]}

KOBAYASHI, Y ^{[1
]}

ARAI, K ^{[1
]}

MINAMI, J ^{[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：

TOTAL SYNTHESIS; QUINOCARCIN; 10-DECARBOXYQUINOCARCIN; ANTITUMOR ANTIBIOTIC; ALDOL COUPLING; DIASTEREOSELECTIVE REDUCTION; INTRAMOLECULAR ANIMAL FORMATION;

D O I：

10.1016/S0040-4020(01)80644-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title synthesis was accomplished by featuring (i) aldol coupling of the 3-methylanisole 11 with 5-substituted- or 3,5-disubstituted 2-formylpyrrolidine 4 or 5, (ii) highly diastereoselective reduction of 1,3-disubstituted isoquinolines 14 and 33 to control stereochemistries at the C5 and C11a positions in 10-decarboxyquinocarcin (2) and quinocarcin (I), respectively, simaultaneously in a single step, and (iii) intramolecular aminal formation of amino aldehydes 21 and 41 to construct the requisite ABCD ring systems 22 and 42 as key steps.

引用

页码：6239 / 6258

页数：20

共 9 条

[1] TOTAL SYNTHESIS OF (-)-QUINOCARCIN AND (-)-10-DECARBOXYQUINOCARCIN
KATOH, T
KIRIHARA, M
NAGATA, Y
KOBAYASHI, Y
ARAI, K
MINAMI, J
TERASHIMA, S
TETRAHEDRON LETTERS, 1993, 34 (36) : 5747 - 5750
[2] 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
[3] 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
[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] EXPEDITIOUS SYNTHESIS OF HIGHLY CYTOTOXIC 10-DECARBOXYQUINOCARCIN AND ITS 7-CYANO CONGENERS FROM QUINOCARCIN
KATOH, T
KIRIHARA, M
YOSHINO, T
TERASHIMA, S
TETRAHEDRON LETTERS, 1993, 34 (36) : 5751 - 5752
[6] 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
[7] ENANTIOSELECTIVE SYNTHESIS OF 5-SUBSTITUTED-2-FORMYLPYRROLIDINE AND 3,5-DISUBSTITUTED-2-FORMYLPYRROLIDINE DERIVATIVES, THE KEY D-RING FRAGMENTS OF (-)-QUINOCARCIN AND (-)-10-DECARBOXYQUINOCARCIN
KATOH, T
NAGATA, Y
KOBAYASHI, Y
ARAI, K
MINAMI, J
TERASHIMA, S
TETRAHEDRON LETTERS, 1993, 34 (36) : 5743 - 5746
[8] SYNTHETIC STUDIES ON APHIDICOLANE AND STEMODANE DITERPENES .4. A STEREOSELECTIVE FORMAL TOTAL SYNTHESIS OF (+/-)-APHIDICOLIN
TANAKA, T
MURAKAMI, K
OKUDA, O
INOUE, T
KURODA, T
KAMEI, K
MURATA, T
YOSHINO, H
IMANISHI, T
KIM, SW
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (02) : 193 - 197
[9] Total synthesis of optically active costaclavine (synthetic studies of indoles and related compounds part 48.)
Osanai, K
Yokoyama, Y
Kondo, K
Murakami, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (11) : 1587 - 1590

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