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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:
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.
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页码:6239 / 6258
页数:20
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