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
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

Carroll, PJ
论文数: 0 引用数: 0
h-index: 0
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.
引用
收藏
页码:3855 / 3857
页数:3
相关论文
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]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7732 - 7739ALAWAR, 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 27695JOSEPH, 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 27695COMINS, 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]. TETRAHEDRON LETTERS, 1993, 34 (33) : 5243 - 5246CASTRO, P论文数: 0 引用数: 0 h-index: 0机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717OVERMAN, LE论文数: 0 引用数: 0 h-index: 0机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717ZHANG, XM论文数: 0 引用数: 0 h-index: 0机构: UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717MARIANO, 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]. TETRAHEDRON-ASYMMETRY, 1998, 9 (24) : 4361 - 4368Chalard, 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, FranceRemuson, 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, FranceGelas-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, FranceGramain, 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]. TETRAHEDRON-ASYMMETRY, 1999, 10 (11) : 2225 - 2235Ciblat, 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, FranceBesse, 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, FranceCanet, 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, FranceTroin, 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, FranceVeschambre, 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, FranceGelas, 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]. TETRAHEDRON LETTERS, 1989, 30 (38) : 5053 - 5056COMINS, 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 84322LAMUNYON, 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]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5807 - 5809COMINS, DL论文数: 0 引用数: 0 h-index: 0机构: Department of Chemistry, North Carolina State University, RaleighLAMUNYON, 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]. CHEMICAL REVIEWS, 2002, 102 (02) : 579 - 601Davis, 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]. ORGANIC LETTERS, 2002, 4 (01) : 103 - 106Davis, BG论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, EnglandMaughan, MAT论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, EnglandChapman, TM论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, EnglandVillard, R论文数: 0 引用数: 0 h-index: 0机构: Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, EnglandCourtney, 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]. HETEROATOM CHEMISTRY, 2002, 13 (05) : 486 - 492Davis, 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 USAChao, 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 USAAndemichael, 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 USAMohanty, 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 USAFang, 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 USABurns, 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 USARao, 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 USASzewczyk, 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]. ORGANIC LETTERS, 2002, 4 (09) : 1599 - 1602Davis, 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 USAFang, 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 USAGoswami, 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