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.
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页码：6239 / 6258
页数：20
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