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.

引用

页码：6239 / 6258

页数：20

共 18 条

[1] TOTAL SYNTHESES OF PHLEICHROME, CALPHOSTIN-A, AND CALPHOSTIN-D - UNUSUAL STEREOSELECTIVE AND STEREOSPECIFIC REACTIONS IN THE SYNTHESIS OF PERYLENEQUINONES [J].