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Regiocontrol in MnIII-mediated oxidative heterobicyclizations:: Access to the core skeletons of oroidin dimers
被引:61
作者
:
Tan, Xianghui
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
Tan, Xianghui
[
1
]
Chen, Chuo
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
Chen, Chuo
[
1
]
机构
:
[1]
Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2006年
/ 45卷
/ 26期
关键词
:
cascade reactions;
natural products;
radical reactions;
rearrangement;
synthetic methods;
D O I
:
10.1002/anie.200601208
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) In control: A cyclization reaction of an allylic β-imidazolinonyl-β-ketoester 1 is carried out in a Mn III-promoted radical cascade. The reaction pathway (5-exo/6-endo or 5-exo/5-exo) can be directed to construct the central cyclopentyl and cyclohexenyl core skeletons (2 and 3) of two classes of oroidin dimers with regiocontrol. An oxidative rearrangement can also be used to convert 2 into 3. PG = protecting group. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4345 / 4348
页数:4
相关论文
共 27 条
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Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation
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Baran, PS
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0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
Li, K
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Li, K
;
O'Malley, DP
论文数:
0
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0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
O'Malley, DP
;
Mitsos, C
论文数:
0
引用数:
0
h-index:
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机构:
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Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
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2006,
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Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin
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h-index:
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O'Malley, DP
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Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
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Zografos, AL
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h-index:
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机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
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O'Malley, DP
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h-index:
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Washington Univ, Dept Chem, St Louis, MO 63130 USA
Washington Univ, Dept Chem, St Louis, MO 63130 USA
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MANGANESE (III) ACETATE INITIATED OXIDATIVE FREE-RADICAL REACTION OF 3-HETEROARYL SUBSTITUTED MALONATES
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0
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0
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Department of Chemistry, National Cheng Kung University
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WANG, SF
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0
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0
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Department of Chemistry, National Cheng Kung University
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0
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Department of Chemistry, National Cheng Kung University, Tainan
CHUANG, CP
;
WANG, SF
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0
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0
h-index:
0
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Department of Chemistry, National Cheng Kung University, Tainan
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.
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1994,
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OXIDATION OF DIETHYL (PYRIDYLMETHYL)MALONATES WITH MN(III) ACETATE, CE(IV) AMMONIUM-NITRATE, AND IRON(III) PERCHLORATE IN THE PRESENCE OF ALKENES AND ALKYNES
[J].
CITTERIO, A
论文数:
0
引用数:
0
h-index:
0
机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
CITTERIO, A
;
SEBASTIANO, R
论文数:
0
引用数:
0
h-index:
0
机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
SEBASTIANO, R
;
CARVAYAL, MC
论文数:
0
引用数:
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机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
CARVAYAL, MC
.
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←
1
2
3
→
共 27 条
[1]
[Anonymous], ANGEW CHEM
[2]
Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation
[J].
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
Li, K
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Li, K
;
O'Malley, DP
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
O'Malley, DP
;
Mitsos, C
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Mitsos, C
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(02)
:249
-252
[3]
Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin
[J].
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
O'Malley, DP
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
O'Malley, DP
;
Zografos, AL
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Zografos, AL
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(20)
:2674
-2677
[4]
Short total synthesis of (±)-sceptrin
[J].
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
;
Zografos, AL
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Zografos, AL
;
O'Malley, DP
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
O'Malley, DP
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(12)
:3726
-3727
[5]
BARAN PS, 2006, ANGEW CHEM, V118, P255
[6]
Synthesis of sceptrin alkaloids
[J].
Birman, VB
论文数:
0
引用数:
0
h-index:
0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA
Washington Univ, Dept Chem, St Louis, MO 63130 USA
Birman, VB
;
Jiang, XT
论文数:
0
引用数:
0
h-index:
0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA
Washington Univ, Dept Chem, St Louis, MO 63130 USA
Jiang, XT
.
ORGANIC LETTERS,
2004,
6
(14)
:2369
-2371
[7]
OXIDATION REACTIONS OF MANGANESE(3) ACETATE .2. FORMATION OF GAMMA-LACTONES FROM OLEFINS AND ACETIC ACID
[J].
BUSH, JB
论文数:
0
引用数:
0
h-index:
0
BUSH, JB
;
FINKBEIN.H
论文数:
0
引用数:
0
h-index:
0
FINKBEIN.H
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1968,
90
(21)
:5903
-&
[8]
MANGANESE (III) ACETATE INITIATED OXIDATIVE FREE-RADICAL REACTION OF 3-HETEROARYL SUBSTITUTED MALONATES
[J].
CHUANG, CP
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, National Cheng Kung University
CHUANG, CP
;
WANG, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, National Cheng Kung University
WANG, SF
.
SYNTHETIC COMMUNICATIONS,
1994,
24
(11)
:1493
-1505
[9]
MANGANESE(III) ACETATE INITIATED OXIDATIVE FREE-RADICAL REACTION BETWEEN N-AROYLINDOLES AND DIMETHYL MALONATE
[J].
CHUANG, CP
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, National Cheng Kung University, Tainan
CHUANG, CP
;
WANG, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, National Cheng Kung University, Tainan
WANG, SF
.
TETRAHEDRON LETTERS,
1994,
35
(08)
:1283
-1284
[10]
OXIDATION OF DIETHYL (PYRIDYLMETHYL)MALONATES WITH MN(III) ACETATE, CE(IV) AMMONIUM-NITRATE, AND IRON(III) PERCHLORATE IN THE PRESENCE OF ALKENES AND ALKYNES
[J].
CITTERIO, A
论文数:
0
引用数:
0
h-index:
0
机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
CITTERIO, A
;
SEBASTIANO, R
论文数:
0
引用数:
0
h-index:
0
机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
SEBASTIANO, R
;
CARVAYAL, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Dipartimento di Chimica del Politecnico, 20133 Milano, P.za L.da Vinci
CARVAYAL, MC
.
JOURNAL OF ORGANIC CHEMISTRY,
1991,
56
(18)
:5335
-5341
←
1
2
3
→