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
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
收藏
页码:6239 / 6258
页数:20
相关论文
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