Asymmetrically induced alkylation of 2-benzyl-4-isopropyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione

被引：12

作者：

Buenadicha, FL ^{[1
]}

Avendaño, C ^{[1
]}

Söllhuber, M ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(98)00464-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The substitution of the 4-methyl group by a 4-isopropyl group in the 2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione system allows a notable improvement in the stereoselective alkylation at C-I. The configuration of the newly introduced stereogenic centre has been assigned on the basis of H-1 NMR data and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4275 / 4284

页数：10

共 23 条

[1] Stereochemical course of acylation and aldol condensation in (4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino-[2,1-b]quinazoline-3,6-diones
Bartolomé, MT
Buenadicha, FL
Avendaño, C
Söllhuber, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (02) : 249 - 258
[2] New findings in the alkylation and N-deprotection of (4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
Buenadicha, FL
Bartolomé, MT
Aguirre, MJ
Avendaño, C
Söllhuber, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (03) : 483 - 501
[3] Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids
Bull, SD
Davies, SG
Epstein, SW
Ouzman, JVA
[J]. CHEMICAL COMMUNICATIONS, 1998, (06) : 659 - 660
[4] DARRIGO MC, 1995, J CHEM RES-S, P162
[5] DEQUESADA AR, COMMUNICATION
[6] GOTTESMAN MM, 1988, J BIOL CHEM, V263, P12163
[7] 5-N-ACETYLARDEEMIN, A NOVEL HETEROCYCLIC COMPOUND WHICH REVERSES MULTIPLE-DRUG RESISTANCE IN TUMOR-CELLS .2. ISOLATION AND ELUCIDATION OF THE STRUCTURE OF 5-N-ACETYLARDEEMIN AND 2 CONGENERS
HOCHLOWSKI, JE
MULLALLY, MM
SPANTON, SG
WHITTERN, DN
HILL, P
MCALPINE, JB
[J]. JOURNAL OF ANTIBIOTICS, 1993, 46 (03) : 380 - 386
[8] 5-N-ACETYLARDEEMIN, A NOVEL HETEROCYCLIC COMPOUND WHICH REVERSES MULTIPLE-DRUG RESISTANCE IN TUMOR-CELLS .1. TAXONOMY AND FERMENTATION OF THE PRODUCING ORGANISM AND BIOLOGICAL-ACTIVITY
KARWOWSKI, JP
JACKSON, M
RASMUSSEN, RR
HUMPHREY, PE
PODDIG, JB
KOHL, WL
SCHERR, MH
KADAM, S
MCALPINE, JB
[J]. JOURNAL OF ANTIBIOTICS, 1993, 46 (03) : 374 - 379
[9] STEREOSELECTIVE TOTAL SYNTHESES OF AMAUROMINE AND 5-N-ACETYLARDEEMIN - A CONCISE ROUTE TO TILE FAMILY OF REVERSE-PRENYLATED HEXAHYDROPYRROLOINDOLE ALKALOIDS
MARSDEN, SP
DEPEW, KM
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) : 11143 - 11144
[10] Regio- and diastereoselective alkylation of 2-substituted 2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
MartinSantamaria, S
Buenadicha, FL
Espada, M
Sollhuber, M
Avendano, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) : 6424 - 6428

← 1 2 3 →