共 26 条
Asymmetric synthesis of functionalized trans-2,6-disubstituted piperidines with N-Sulfinyl δ-amino β-ketoesters.: Synthesis of (-)-lasubine I
被引:63
作者:

Davis, FA
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机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

Rao, A
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机构: Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

Carroll, PJ
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机构: Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
机构:
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词:
D O I:
10.1021/ol035390j
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
[GRAPHICS] The hydroxy-directed reduction of 1,2-dehydropiperidines with the "ate" complex of DIBAL-H and n-BuLi affords functionalized trans-2,6-disubstituted piperidines. This methodology was employed in the asymmetric synthesis of the quinolizidine alkaloid (-)-lasubine I.
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页码:3855 / 3857
页数:3
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共 26 条
[1]
CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT - SYNTHESIS OF (-)-CONIINE AND (PLUS-OR-MINUS)-LUPININE
[J].
ALAWAR, RS
;
JOSEPH, SP
;
COMINS, DL
.
JOURNAL OF ORGANIC CHEMISTRY,
1993, 58 (27)
:7732-7739

ALAWAR, RS
论文数: 0 引用数: 0
h-index: 0
机构:
N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695 N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695

JOSEPH, SP
论文数: 0 引用数: 0
h-index: 0
机构:
N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695 N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695

COMINS, DL
论文数: 0 引用数: 0
h-index: 0
机构:
N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695 N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695
[2]
PREPARATION OF ENANTIOENRICHED TETRAHYDROPYRIDINES BY IMINIUM ION-VINYLSILANE CYCLIZATIONS
[J].
CASTRO, P
;
OVERMAN, LE
;
ZHANG, XM
;
MARIANO, PS
.
TETRAHEDRON LETTERS,
1993, 34 (33)
:5243-5246

CASTRO, P
论文数: 0 引用数: 0
h-index: 0
机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

OVERMAN, LE
论文数: 0 引用数: 0
h-index: 0
机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

ZHANG, XM
论文数: 0 引用数: 0
h-index: 0
机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

MARIANO, PS
论文数: 0 引用数: 0
h-index: 0
机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
[3]
Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)-lasubine II and (+)-subcosine II
[J].
Chalard, P
;
Remuson, R
;
Gelas-Mialhe, Y
;
Gramain, JC
.
TETRAHEDRON-ASYMMETRY,
1998, 9 (24)
:4361-4368

Chalard, P
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France

Remuson, R
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France

Gelas-Mialhe, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France

Gramain, JC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France
[4]
A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines
[J].
Ciblat, S
;
Besse, P
;
Canet, JL
;
Troin, Y
;
Veschambre, H
;
Gelas, J
.
TETRAHEDRON-ASYMMETRY,
1999, 10 (11)
:2225-2235

Ciblat, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

Besse, P
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

Canet, JL
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

Troin, Y
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

Veschambre, H
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

Gelas, J
论文数: 0 引用数: 0
h-index: 0
机构: Univ Blaise Pascal, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France
[5]
PREPARATION OF 1-(TERT-BUTOXYCARBONYL)-2,6-DIALKYL-2,3-DIHYDRO-4-PYRIDONES - A STEREOCONTROLLED SYNTHESIS OF (+/-)-MYRTINE
[J].
COMINS, DL
;
LAMUNYON, DH
.
TETRAHEDRON LETTERS,
1989, 30 (38)
:5053-5056

COMINS, DL
论文数: 0 引用数: 0
h-index: 0
机构:
UTAH STATE UNIV,DEPT CHEM & BIOCHEM,LOGAN,UT 84322 UTAH STATE UNIV,DEPT CHEM & BIOCHEM,LOGAN,UT 84322

LAMUNYON, DH
论文数: 0 引用数: 0
h-index: 0
机构:
UTAH STATE UNIV,DEPT CHEM & BIOCHEM,LOGAN,UT 84322 UTAH STATE UNIV,DEPT CHEM & BIOCHEM,LOGAN,UT 84322
[6]
ENANTIOPURE 2,3-DIHYDRO-4-PYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC SYNTHESES OF THE QUINOLIZIDINE ALKALOIDS (+)-MYRTINE, (-)-LASUBINE-I, AND (+)-SUBCOSINE-I
[J].
COMINS, DL
;
LAMUNYON, DH
.
JOURNAL OF ORGANIC CHEMISTRY,
1992, 57 (22)
:5807-5809

COMINS, DL
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, North Carolina State University, Raleigh

LAMUNYON, DH
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, North Carolina State University, Raleigh
[7]
Synthesis of glycoproteins
[J].
Davis, BG
.
CHEMICAL REVIEWS,
2002, 102 (02)
:579-601

Davis, BG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[8]
Novel cyclic sugar imines: Carbohydrate mimics and easily elaborated scaffolds for aza-sugars
[J].
Davis, BG
;
Maughan, MAT
;
Chapman, TM
;
Villard, R
;
Courtney, S
.
ORGANIC LETTERS,
2002, 4 (01)
:103-106

Davis, BG
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

Maughan, MAT
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

Chapman, TM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

Villard, R
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

Courtney, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[9]
Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
[J].
Davis, FA
;
Chao, B
;
Andemichael, YW
;
Mohanty, PK
;
Fang, TN
;
Burns, DM
;
Rao, A
;
Szewczyk, JM
.
HETEROATOM CHEMISTRY,
2002, 13 (05)
:486-492

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

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

Andemichael, YW
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

Mohanty, PK
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

Fang, TN
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

Burns, DM
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
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

Szewczyk, JM
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
[10]
Asymmetric synthesis of substituted prolines from δ-amino β-ketoesters.: Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate
[J].
Davis, FA
;
Fang, TN
;
Goswami, R
.
ORGANIC LETTERS,
2002, 4 (09)
:1599-1602

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

Fang, TN
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

Goswami, R
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