SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN

被引：18
|
作者：
SAITO, S [1 ]
TAMURA, O [1 ]
KOBAYASHI, Y [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; ABE RING SYSTEM; DIASTEREOSELECTIVE REDUCTION; 4-O-BENZYL-2,3-O-ISOPROPYLIDENETHREOSE;
D O I：
10.1016/S0040-4020(01)80641-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantiomeric pairs of the ABE ring system (5 and ent-5) and its analogues (6, ent-6, 7, and ent-7) of quinocarcin (1), a prominent antitumor antibiotic, were synthesized in >95% ee with an aim to elucidate structure-activity relationships of 1. The key step of the synthesis includes novel diastereoselective reduction of 3,4-dihydroisoquinoline derivatives 25 and ent-25, wherein each enantiomer of 4-O-benzyl-2,3-O-isopropylidene-threose (I and ent-I) is employed as a chiral auxiliary.
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页码：6193 / 6208
页数：16
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