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.

引用

页码：6193 / 6208

页数：16

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