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Addition of metallo enolates to chiral 1-acylpyridinium salts: Total synthesis of (+)-cannabisativine
被引:70
作者
:
Kuethe, JT
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Kuethe, JT
[
1
]
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
[
1
]
机构
:
[1]
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
来源
:
ORGANIC LETTERS
|
2000年
/ 2卷
/ 06期
关键词
:
D O I
:
10.1021/ol0056271
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
A novel route to the first asymmetric synthesis of (+)-cannabisativine (1) is described. The total synthesis of 1 was accomplished with a high degree of regio- and stereoselectivity in 19 steps and 9% overall yield.
引用
收藏
页码:855 / 857
页数:3
相关论文
共 16 条
[1]
TOTAL SYNTHESIS OF ANHYDROCANNABISATIVENE
[J].
BAILEY, TR
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
BAILEY, TR
;
GARIGIPATI, RS
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
GARIGIPATI, RS
;
MORTON, JA
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
MORTON, JA
;
WEINREB, SM
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
WEINREB, SM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1984,
106
(11)
:3240
-3245
[2]
THE STRUCTURE AND FUNCTION OF ESTROGENS .9. SYNTHESIS OF THE TRANS ISOMER OF 5,5,10B-TRIMETHYL-4B,5,6,10B,11,12-HEXAHYDROCHRYSENE-2,8-DIOL
[J].
COLLINS, DJ
论文数:
0
引用数:
0
h-index:
0
COLLINS, DJ
;
CULLEN, JD
论文数:
0
引用数:
0
h-index:
0
CULLEN, JD
.
AUSTRALIAN JOURNAL OF CHEMISTRY,
1988,
41
(05)
:735
-744
[3]
EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL
[J].
COMINS, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
COMINS, DL
;
SALVADOR, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
SALVADOR, JM
.
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(17)
:4656
-4661
[4]
ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS
[J].
COMINS, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
COMINS, DL
;
JOSEPH, SP
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
JOSEPH, SP
;
GOEHRING, RR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
GOEHRING, RR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(11)
:4719
-4728
[5]
Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts
[J].
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
;
Kuethe, JT
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Kuethe, JT
;
Hong, H
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Hong, H
;
Lakner, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Lakner, FJ
;
Concolino, TE
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Concolino, TE
;
Rheingold, AL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Rheingold, AL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(11)
:2651
-2652
[6]
A CHIRAL SYNTHESIS OF (-)-CANNABISATIVINE - AN APPLICATION OF THE HIGHLY DIASTEREOSELECTIVE HETERO-DIELS-ALDER REACTION
[J].
HAMADA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
HAMADA, T
;
ZENKOH, T
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
ZENKOH, T
;
SATO, H
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
SATO, H
;
YONEMITSU, O
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
YONEMITSU, O
.
TETRAHEDRON LETTERS,
1991,
32
(13)
:1649
-1652
[7]
BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS
[J].
IVERSEN, T
论文数:
0
引用数:
0
h-index:
0
机构:
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
IVERSEN, T
;
BUNDLE, DR
论文数:
0
引用数:
0
h-index:
0
机构:
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
BUNDLE, DR
.
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1981,
(23)
:1240
-1241
[8]
The Mukaiyama-Michael reaction of N-acyl-2,3-dihydro-4-pyridones:: Regio- and stereoselective synthesis of cis-2,6-disubstituted 1,2,5,6-tetrahydropyridines
[J].
Kuethe, JT
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Kuethe, JT
;
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
.
ORGANIC LETTERS,
1999,
1
(07)
:1031
-1033
[9]
A NEW METHOD FOR THE PREPARATION OF 3-SUBSTITUTED-2-OXAZOLIDONES
[J].
LESHER, GY
论文数:
0
引用数:
0
h-index:
0
LESHER, GY
;
SURREY, AR
论文数:
0
引用数:
0
h-index:
0
SURREY, AR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1955,
77
(03)
:636
-641
[10]
LOTTER HL, 1975, TETRAHEDRON LETT, P2815
←
1
2
→
共 16 条
[1]
TOTAL SYNTHESIS OF ANHYDROCANNABISATIVENE
[J].
BAILEY, TR
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
BAILEY, TR
;
GARIGIPATI, RS
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
GARIGIPATI, RS
;
MORTON, JA
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
MORTON, JA
;
WEINREB, SM
论文数:
0
引用数:
0
h-index:
0
机构:
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
WEINREB, SM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1984,
106
(11)
:3240
-3245
[2]
THE STRUCTURE AND FUNCTION OF ESTROGENS .9. SYNTHESIS OF THE TRANS ISOMER OF 5,5,10B-TRIMETHYL-4B,5,6,10B,11,12-HEXAHYDROCHRYSENE-2,8-DIOL
[J].
COLLINS, DJ
论文数:
0
引用数:
0
h-index:
0
COLLINS, DJ
;
CULLEN, JD
论文数:
0
引用数:
0
h-index:
0
CULLEN, JD
.
AUSTRALIAN JOURNAL OF CHEMISTRY,
1988,
41
(05)
:735
-744
[3]
EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL
[J].
COMINS, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
COMINS, DL
;
SALVADOR, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
SALVADOR, JM
.
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(17)
:4656
-4661
[4]
ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS
[J].
COMINS, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
COMINS, DL
;
JOSEPH, SP
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
JOSEPH, SP
;
GOEHRING, RR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, North Carolina State University, Raleigh
GOEHRING, RR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(11)
:4719
-4728
[5]
Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts
[J].
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
;
Kuethe, JT
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Kuethe, JT
;
Hong, H
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Hong, H
;
Lakner, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Lakner, FJ
;
Concolino, TE
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Concolino, TE
;
Rheingold, AL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Rheingold, AL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(11)
:2651
-2652
[6]
A CHIRAL SYNTHESIS OF (-)-CANNABISATIVINE - AN APPLICATION OF THE HIGHLY DIASTEREOSELECTIVE HETERO-DIELS-ALDER REACTION
[J].
HAMADA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
HAMADA, T
;
ZENKOH, T
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
ZENKOH, T
;
SATO, H
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
SATO, H
;
YONEMITSU, O
论文数:
0
引用数:
0
h-index:
0
机构:
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
YONEMITSU, O
.
TETRAHEDRON LETTERS,
1991,
32
(13)
:1649
-1652
[7]
BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS
[J].
IVERSEN, T
论文数:
0
引用数:
0
h-index:
0
机构:
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
IVERSEN, T
;
BUNDLE, DR
论文数:
0
引用数:
0
h-index:
0
机构:
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
NATL RES COUNCIL CANADA,DIV BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
BUNDLE, DR
.
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1981,
(23)
:1240
-1241
[8]
The Mukaiyama-Michael reaction of N-acyl-2,3-dihydro-4-pyridones:: Regio- and stereoselective synthesis of cis-2,6-disubstituted 1,2,5,6-tetrahydropyridines
[J].
Kuethe, JT
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Kuethe, JT
;
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
.
ORGANIC LETTERS,
1999,
1
(07)
:1031
-1033
[9]
A NEW METHOD FOR THE PREPARATION OF 3-SUBSTITUTED-2-OXAZOLIDONES
[J].
LESHER, GY
论文数:
0
引用数:
0
h-index:
0
LESHER, GY
;
SURREY, AR
论文数:
0
引用数:
0
h-index:
0
SURREY, AR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1955,
77
(03)
:636
-641
[10]
LOTTER HL, 1975, TETRAHEDRON LETT, P2815
←
1
2
→