A new route toward 4-substituted pyrazino[2,1-b] qiuinazoline-3,6-dione systems.: Total synthesis of glyantrypine

被引：32

作者：

Cledera, P ^{[1
]}

Avendaño, C ^{[1
]}

Menéndez, JC ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 06期

关键词：

D O I：

10.1021/jo991626e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

引用

页码：1743 / 1749

页数：7

共 37 条

[1] BAILEY PD, 1995, COMPREHENSIVE FUNCTI
[2] TOTAL SYNTHESIS OF NONPEPTIDAL CHOLECYSTOKININ ANTAGONISTS FROM ASPERGILLUS-ALLIACEUS
BOCK, MG
DIPARDO, RM
PITZENBERGER, SM
HOMNICK, CF
SPRINGER, JP
FREIDINGER, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) : 1644 - 1646
[3] 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
[4] AMNESIA-REVERSAL ACTIVITY OF A SERIES OF CYCLIC IMIDES
BUTLER, DE
LEONARD, JD
CAPRATHE, BW
LITALIEN, YJ
PAVIA, MR
HERSHENSON, FM
POSCHEL, PH
MARRIOTT, JG
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (03) : 498 - 503
[5] Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
Cledera, P
Avendaño, C
Menéndez, JC
[J]. TETRAHEDRON, 1998, 54 (40) : 12349 - 12360
[6] Fujimoto H, 1996, CHEM PHARM BULL, V44, P1843, DOI 10.1248/cpb.44.1843
[7] KETOMETHYLENE AND (CYANOMETHYLENE)AMINO PSEUDOPEPTIDE ANALOGS OF THE C-TERMINAL HEXAPEPTIDE OF NEUROTENSIN
GONZALEZMUNIZ, R
GARCIALOPEZ, MT
GOMEZMONTERREY, I
HERRANZ, R
JIMENO, ML
SUAREZGEA, ML
JOHANSEN, NL
MADSEN, K
THOGERSEN, H
SUZDAK, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) : 1015 - 1021
[8] Synthesis of (-)-alantrypinone
Hart, DJ
Magomedov, N
[J]. TETRAHEDRON LETTERS, 1999, 40 (30) : 5429 - 5432
[9] Total syntheses of (-)-asperlicin and (-)-asperlicin C
He, F
Foxman, BM
Snider, BB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) : 6417 - 6418
[10] He F, 1997, SYNLETT, P483

← 1 2 3 4 →