SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .2. SYNTHESIS OF AN ENANTIOMERIC PAIR OF THE ABC RING-SYSTEM OF QUINOCARCIN

被引：15

作者：

SAITO, S ^{[1
]}

TANAKA, K ^{[1
]}

NAKATANI, K ^{[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; ABC RING SYSTEM; DIASTEREOSELECTIVE REDUCTION; INTRAMOLECULAR N; O-ACETAL FORMATION;

D O I：

10.1016/S0040-4020(01)80642-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiomeric pair of the ABC ring system (5 and ent-5) of quinocarcin (1), a patent antitumor antibiotic, was synthesized in >95% ee with an. aim to disclose novel aspects of the structure-activity relationships of 1. The key features of the synthesis consist of novel diastereoselective reduction of 1,3-disubstituted isoquinoline derivatives 29 and ent-29 to control stereochemistries at the C6 and C11a positions in 5 and ent-5 simultaneously in a single step and intramolecular N,O-acetal formation of amino aldehydes 6 and ent-6 to complete the requisite skeletal framework.

引用

页码：6209 / 6220

页数：12

共 18 条

[1]

BICHAUT P, 1969, CR ACAD SCI C CHIM, V269, P1550

[2] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].