共 23 条
Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C
被引:120
作者:

Fuchs, JR
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机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA

Funk, RL
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机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA
机构:
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词:
D O I:
10.1021/ol047532v
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A variety of 3,3-disubstituted 2-indolinones have been prepared by treatment of 3-bromo-3-alkyl-2-indolinones with dienophiles/nucleophiles in the presence of cesium carbonate. Application of this general strategy has facilitated the total syntheses of the reverse prenylated marine natural products (+/-)-flustramine A and (+/-)-flustramine C.
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页码:677 / 680
页数:4
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[1]
MARINE ALKALOIDS .3. BROMO-SUBSTITUTED ALKALOIDS FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA, FLUSTRAMINE-C AND FLUSTRAMINOL-A AND FLUSTRAMINOL-B
[J].
CARLE, JS
;
CHRISTOPHERSEN, C
.
JOURNAL OF ORGANIC CHEMISTRY,
1981, 46 (17)
:3440-3443

CARLE, JS
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV COPENHAGEN, HC ORSTED INST, DEPT GEN & ORGAN CHEM, MARINE CHEM SECT, DK-2100 COPENHAGEN, DENMARK UNIV COPENHAGEN, HC ORSTED INST, DEPT GEN & ORGAN CHEM, MARINE CHEM SECT, DK-2100 COPENHAGEN, DENMARK

CHRISTOPHERSEN, C
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV COPENHAGEN, HC ORSTED INST, DEPT GEN & ORGAN CHEM, MARINE CHEM SECT, DK-2100 COPENHAGEN, DENMARK UNIV COPENHAGEN, HC ORSTED INST, DEPT GEN & ORGAN CHEM, MARINE CHEM SECT, DK-2100 COPENHAGEN, DENMARK
[2]
MARINE ALKALOIDS .2. BROMO ALKALOIDS FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA - ISOLATION AND STRUCTURE ELUCIDATION
[J].
CARLE, JS
;
CHRISTOPHERSEN, C
.
JOURNAL OF ORGANIC CHEMISTRY,
1980, 45 (09)
:1586-1589

CARLE, JS
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV COPENHAGEN,HC ORSTED INST,MARINE CHEM SECT,CHEM LAB 2,DK-2100 COPENHAGEN O,DENMARK UNIV COPENHAGEN,HC ORSTED INST,MARINE CHEM SECT,CHEM LAB 2,DK-2100 COPENHAGEN O,DENMARK

CHRISTOPHERSEN, C
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV COPENHAGEN,HC ORSTED INST,MARINE CHEM SECT,CHEM LAB 2,DK-2100 COPENHAGEN O,DENMARK UNIV COPENHAGEN,HC ORSTED INST,MARINE CHEM SECT,CHEM LAB 2,DK-2100 COPENHAGEN O,DENMARK
[3]
Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents
[J].
Depew, KM
;
Marsden, SP
;
Zatorska, D
;
Zatorski, A
;
Bornmann, WG
;
Danishefsky, SJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999, 121 (51)
:11953-11963

Depew, KM
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA

Marsden, SP
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA

Zatorska, D
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA

Zatorski, A
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA

Bornmann, WG
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA

Danishefsky, SJ
论文数: 0 引用数: 0
h-index: 0
机构: Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem & Preparat Synthesis Core Facil, New York, NY 10021 USA
[4]
Total synthesis of (±)-perophoramidine
[J].
Fuchs, JR
;
Funk, RL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004, 126 (16)
:5068-5069

Fuchs, JR
论文数: 0 引用数: 0
h-index: 0
机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA

Funk, RL
论文数: 0 引用数: 0
h-index: 0
机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA
[5]
Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines
[J].
Fuchs, JR
;
Funk, RL
.
ORGANIC LETTERS,
2001, 3 (21)
:3349-3351

Fuchs, JR
论文数: 0 引用数: 0
h-index: 0
机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA

Funk, RL
论文数: 0 引用数: 0
h-index: 0
机构:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ, Dept Chem, University Pk, PA 16802 USA
[6]
2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES
[J].
FUKUYAMA, T
;
JOW, CK
;
CHEUNG, M
.
TETRAHEDRON LETTERS,
1995, 36 (36)
:6373-6374

FUKUYAMA, T
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Rice University, Houston

JOW, CK
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Rice University, Houston

CHEUNG, M
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Rice University, Houston
[7]
2-AZA-2,4-CYCLOPENTADIENONE - EXISTENCE AND REACTIVITY
[J].
GAVINA, F
;
COSTERO, AM
;
ANDREU, MR
;
CARDA, M
;
LUIS, SV
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988, 110 (12)
:4017-4018

GAVINA, F
论文数: 0 引用数: 0
h-index: 0

COSTERO, AM
论文数: 0 引用数: 0
h-index: 0

ANDREU, MR
论文数: 0 引用数: 0
h-index: 0

CARDA, M
论文数: 0 引用数: 0
h-index: 0

LUIS, SV
论文数: 0 引用数: 0
h-index: 0
[8]
REACTIONS OF 3-BROMOOXINDOLES - SYNTHESIS OF 3-METHYLENEOXINDOLE
[J].
HINMAN, RL
;
BAUMAN, CP
.
JOURNAL OF ORGANIC CHEMISTRY,
1964, 29 (08)
:2431-&

HINMAN, RL
论文数: 0 引用数: 0
h-index: 0

BAUMAN, CP
论文数: 0 引用数: 0
h-index: 0
[9]
A Suzuki coupling method for directly introducing a protected β-aminoethyl group into arenes and alkenes.: Convenient synthesis of phenethyl and homoallylic amines
[J].
Kamatani, A
;
Overman, LE
.
JOURNAL OF ORGANIC CHEMISTRY,
1999, 64 (23)
:8743-8744

Kamatani, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Overman, LE
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
[10]
A short route to ''reverse-prenylated'' pyrrolo[2,3-b]indoles via tandem olefination and Claisen rearrangement of 2-(3,3-dimethylallyloxy)indol-3-ones: First total synthesis of flustramine C
[J].
Kawasaki, T
;
Terashima, R
;
Sakaguchi, K
;
Sekiguchi, H
;
Sakamoto, M
.
TETRAHEDRON LETTERS,
1996, 37 (42)
:7525-7528

Kawasaki, T
论文数: 0 引用数: 0
h-index: 0
机构:
MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN

Terashima, R
论文数: 0 引用数: 0
h-index: 0
机构:
MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN

Sakaguchi, K
论文数: 0 引用数: 0
h-index: 0
机构:
MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN

Sekiguchi, H
论文数: 0 引用数: 0
h-index: 0
机构:
MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN

Sakamoto, M
论文数: 0 引用数: 0
h-index: 0
机构:
MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN