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Protecting-Group-Free Total Synthesis of (±)-Subincanadine F
被引:40
作者
:
Chen, Pinhong
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Chen, Pinhong
[
1
]
Cao, Lidong
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Cao, Lidong
[
1
]
Li, Chaozhong
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
Li, Chaozhong
[
1
]
机构
:
[1]
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, Shanghai 200032, Peoples R China
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
2009年
/ 74卷
/ 19期
基金
:
中国国家自然科学基金;
关键词
:
ASYMMETRIC-SYNTHESIS;
MANNICH REACTION;
ALDOL ADDITIONS;
ALDEHYDES;
D O I
:
10.1021/jo901444e
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
With chemoselective Dieckmann condensation as the key step, the protective-group-free total synthesis of (+/-)-subincanadine F was accomplished in 7 steps from the commercially available tryptamine in 33% overall yield.
引用
收藏
页码:7533 / 7535
页数:3
相关论文
共 26 条
[1]
Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
ORGANIC LETTERS,
2000,
2
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777
[2]
Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich Cyclization and n-sulfinyl δ-amino β-ketoesters
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Mang, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Mang, Y
Anilkumar, G
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Anilkumar, G
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
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8064
[3]
Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Chao, B
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Chao, B
Rao, A
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Rao, A
[J].
ORGANIC LETTERS,
2001,
3
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3171
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A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide ORL-1 receptor antagonist
论文数:
引用数:
h-index:
机构:
De Risi, C
Pollini, GP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Pollini, GP
Trapella, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Trapella, C
Peretto, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Peretto, I
Ronzoni, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Ronzoni, S
Giardina, GAM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Giardina, GAM
[J].
BIOORGANIC & MEDICINAL CHEMISTRY,
2001,
9
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: 1871
-
1877
[5]
STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
EVANS, DA
RIEGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
RIEGER, DL
BILODEAU, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
BILODEAU, MT
URPI, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
URPI, F
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
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: 1047
-
1049
[6]
FLEMING L, 1992, J CHEM SOC P1, P3351
[7]
Total synthesis of indole alkaloid (±)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction
Gao, Peng
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Gao, Peng
Liu, Yanqin
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Liu, Yanqin
Zhang, Lei
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Zhang, Lei
Xu, Peng-Fei
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Xu, Peng-Fei
Wang, Shaowu
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Wang, Shaowu
Lu, Yong
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Lu, Yong
He, Mingyuan
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
He, Mingyuan
Zhai, Hongbin
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Zhai, Hongbin
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2006,
71
(25)
: 9495
-
9498
[8]
A novel and facile preparation of bremazocine enantiomers through optically pure N-norbremazocines
Greiner, E
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Greiner, E
Folk, JE
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Folk, JE
Jacobson, AE
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Jacobson, AE
Rice, KC
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Rice, KC
[J].
BIOORGANIC & MEDICINAL CHEMISTRY,
2004,
12
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: 233
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238
[9]
Protecting-group-free synthesis
Hoffmann, Reinhard W.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
Hoffmann, Reinhard W.
[J].
SYNTHESIS-STUTTGART,
2006,
(21):
: 3531
-
3541
[10]
Structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 via catalytic asymmetric Nozaki-Hiyama reactions
Inoue, Masahiro
论文数:
0
引用数:
0
h-index:
0
机构:
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Inoue, Masahiro
Nakada, Masahisa
论文数:
0
引用数:
0
h-index:
0
机构:
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Nakada, Masahisa
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(14)
: 4164
-
+
←
1
2
3
→
共 26 条
[1]
Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
ORGANIC LETTERS,
2000,
2
(06)
: 775
-
777
[2]
Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich Cyclization and n-sulfinyl δ-amino β-ketoesters
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Mang, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Mang, Y
Anilkumar, G
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Anilkumar, G
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(21)
: 8061
-
8064
[3]
Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Chao, B
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Chao, B
Rao, A
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Rao, A
[J].
ORGANIC LETTERS,
2001,
3
(20)
: 3169
-
3171
[4]
A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide ORL-1 receptor antagonist
论文数:
引用数:
h-index:
机构:
De Risi, C
Pollini, GP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Pollini, GP
Trapella, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Trapella, C
Peretto, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Peretto, I
Ronzoni, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Ronzoni, S
Giardina, GAM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
Giardina, GAM
[J].
BIOORGANIC & MEDICINAL CHEMISTRY,
2001,
9
(07)
: 1871
-
1877
[5]
STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
EVANS, DA
RIEGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
RIEGER, DL
BILODEAU, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
BILODEAU, MT
URPI, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University Cambridge
URPI, F
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
(03)
: 1047
-
1049
[6]
FLEMING L, 1992, J CHEM SOC P1, P3351
[7]
Total synthesis of indole alkaloid (±)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction
Gao, Peng
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Gao, Peng
Liu, Yanqin
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Liu, Yanqin
Zhang, Lei
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Zhang, Lei
Xu, Peng-Fei
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Xu, Peng-Fei
Wang, Shaowu
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Wang, Shaowu
Lu, Yong
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Lu, Yong
He, Mingyuan
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
He, Mingyuan
Zhai, Hongbin
论文数:
0
引用数:
0
h-index:
0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
Zhai, Hongbin
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2006,
71
(25)
: 9495
-
9498
[8]
A novel and facile preparation of bremazocine enantiomers through optically pure N-norbremazocines
Greiner, E
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Greiner, E
Folk, JE
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Folk, JE
Jacobson, AE
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Jacobson, AE
Rice, KC
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
NIDDKD, Med Chem Lab, US Dept HHS, NIH, Bethesda, MD 20892 USA
Rice, KC
[J].
BIOORGANIC & MEDICINAL CHEMISTRY,
2004,
12
(01)
: 233
-
238
[9]
Protecting-group-free synthesis
Hoffmann, Reinhard W.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
Hoffmann, Reinhard W.
[J].
SYNTHESIS-STUTTGART,
2006,
(21):
: 3531
-
3541
[10]
Structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 via catalytic asymmetric Nozaki-Hiyama reactions
Inoue, Masahiro
论文数:
0
引用数:
0
h-index:
0
机构:
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Inoue, Masahiro
Nakada, Masahisa
论文数:
0
引用数:
0
h-index:
0
机构:
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Waseda Univ, Fac Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
Nakada, Masahisa
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(14)
: 4164
-
+
←
1
2
3
→