AN IMPROVED SYNTHESIS OF 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) - A SIMPLIFIED ANALOG OF THE CC-1065 ALKYLATION SUBUNIT

被引：101

作者：

BOGER, DL ^{[1
]}

YUN, WY ^{[1
]}

TEEGARDEN, BR ^{[1
]}

机构：

[1] SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 10期

关键词：

D O I：

10.1021/jo00036a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and improved synthesis of 11, the immediate precursor to N-BOC-CBI and related analogues of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one alkylation subunit, is detailed based on a direct 5-exo-trig aryl radical-alkene cyclization for 3-hydroxymethylindoline generation.

引用

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页码：2873 / 2876

页数：4

相关论文

共 40 条

[1] CC-1065 PARTIAL STRUCTURES - ENHANCEMENT OF NONCOVALENT AFFINITY FOR DNA MINOR GROOVE BINDING THROUGH INTRODUCTION OF STABILIZING ELECTROSTATIC INTERACTIONS [J].

BOGER, DL ;

SAKYA, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1277-1284

[2] DEMONSTRATION OF A PRONOUNCED EFFECT OF NONCOVALENT BINDING SELECTIVITY ON THE (+)-CC-1065 DNA ALKYLATION AND IDENTIFICATION OF THE PHARMACOPHORE OF THE ALKYLATION SUBUNIT [J].

BOGER, DL ;

ZARRINMAYEH, H ;

MUNK, SA ;

KITOS, PA ;

SUNTORNWAT, O .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (04) :1431-1435

[3] A DEMONSTRATION OF THE INTRINSIC IMPORTANCE OF STABILIZING HYDROPHOBIC BINDING AND NONCOVALENT VANDERWAALS CONTACTS DOMINANT IN THE NONCOVALENT CC-1065/B-DNA BINDING [J].

BOGER, DL ;

INVERGO, BJ ;

COLEMAN, RS ;

ZARRINMAYEH, H ;

KITOS, PA ;

THOMPSON, SC ;

LEONG, T ;

MCLAUGHLIN, LW .

CHEMICO-BIOLOGICAL INTERACTIONS, 1990, 73 (01) :29-52

[4] (+)-CC-1065 DNA ALKYLATION - KEY STUDIES DEMONSTRATING A NONCOVALENT BINDING SELECTIVITY CONTRIBUTION TO THE ALKYLATION SELECTIVITY [J].

BOGER, DL ;

MUNK, SA ;

ZARRINMAYEH, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3980-3983

[5] SYNTHESIS OF N-(TERT-BUTYLOXYCARBONYL)-CBI, CBI, CBI-CDPI1, AND CBI-CDPI2 - ENHANCED FUNCTIONAL ANALOGS OF CC-1065 INCORPORATING THE 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].

BOGER, DL ;

ISHIZAKI, T ;

KITOS, PA ;

SUNTORNWAT, O .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5823-5832

[6]

BOGER DL, 1991, HETEROCYCLES IN BIO-ORGANIC CHEMISTRY, P103

[7] RESOLUTION OF A CBI PRECURSOR AND INCORPORATION INTO THE SYNTHESIS OF (+)-CBI, (+)-CBI-CDPI1, (+)-CBI-CDPI2 - ENHANCED FUNCTIONAL ANALOGS OF (+)-CC-1065 - A CRITICAL-APPRAISAL OF A PROPOSED RELATIONSHIP BETWEEN ELECTROPHILE REACTIVITY, DNA-BINDING PROPERTIES, AND CYTOTOXIC POTENCY [J].

BOGER, DL ;

ISHIZAKI, T .

TETRAHEDRON LETTERS, 1990, 31 (06) :793-796

[8] SYNTHESIS AND PRELIMINARY EVALUATION OF AGENTS INCORPORATING THE PHARMACOPHORE OF THE DUOCARMYCIN PYRINDAMYCIN ALKYLATION SUBUNIT - IDENTIFICATION OF THE CC-1065 DUOCARMYCIN COMMON PHARMACOPHORE [J].

BOGER, DL ;

ISHIZAKI, T ;

ZARRINMAYEH, H ;

KITOS, PA ;

SUNTORNWAT, O .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4499-4502

[9] SYNTHESIS OF N-(PHENYLSULFONYL)-CI, N-((TERT-BUTYLOXY)CARBONYL)-CI, CI-CDPI1, AND CI-CDPI2 - CC-1065 FUNCTIONAL ANALOGS INCORPORATING THE PARENT 1,2,7,7A-TETRAHYDROCYCLOPROP[1,2-C]INDOL-4-ONE (CI) LEFT-HAND SUBUNIT [J].

BOGER, DL ;

WYSOCKI, RJ ;

ISHIZAKI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5230-5240

[10] TOTAL SYNTHESIS AND EVALUATION OF (+/-)-N-(TERT-BUTYLOXYCARBONYL)-CBI, (+/-)-CBI-CDPI1, AND (+/-)-CBI-CDPI2 - CC-1065 FUNCTIONAL AGENTS INCORPORATING THE EQUIVALENT 1,2,9,9A-TETRAHYDROCYCLOPROP[1,2-C]BENZ[1,2-E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].

BOGER, DL ;

ISHIZAKI, T ;

WYSOCKI, RJ ;

MUNK, SA ;

KITOS, PA ;

SUNTORNWAT, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6461-6463

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