SYNTHESES OF 1-OXAQUINOLIZIDINES VIA REDUCTIVE CYCLIZATION OF HYDROXY-LACTAMS

被引：19

作者：

AHN, KH ^{[1
]}

LEE, SJ ^{[1
]}

机构：

[1] POHANG INST SCI & TECHNOL,CTR BIOFUNCT MOLEC,POHANG 790600,SOUTH KOREA

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 04期

关键词：

1-OXAQUINOLIZIDINE; IMINIUM ION; ATE COMPLEX FROM DIBAL AND N-BULI; XESTOSPONGIN A; IMINIUM ION-ENAMINE TAUTOMERISM;

D O I：

10.1016/S0040-4039(00)93981-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the 1-oxaquinolizidine moiety of xestospongin A via reductive iminium ion formation from a lactam is described.

引用

页码：507 / 510

页数：4

共 18 条

[1]

BAZANT V, 1968, TETRAHEDRON LETT, V9, P3303

[2] ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIN-DERIVATEN [J].

BOHLMANN, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1957, 69 (20) :641-642

[3] SELECTIVE REDUCTIONS .16. REACTION OF DISIAMYLBORANE IN TETRAHYDROFURAN WITH SELECTED ORGANIC COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL GROUPS [J].

BROWN, HC ;

BIGLEY, DB ;

ARORA, SK ;

YOON, NM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (24) :7161-&

[4] SELECTIVE REDUCTIONS .V. PARTIAL RED1CTION OF TERTIARY AMIDES BY LITHIUM DI- + TRIETHOXYALUMINOHYDRIDES-NEW ALDEHYDE SYNTHESIS VIA DIMETHYLAMIDES [J].

BROWN, HC ;

TSUKAMOTO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1089-&

[5] CLO2 OXIDATION OF AMINES - SYNTHETIC UTILITY AND A BIOMIMETIC SYNTHESIS OF ELAEOCARPIDINE [J].

CHEN, CK ;

HORTMANN, AG ;

MARZABADI, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4829-4831

[6] THERMODYNAMIC CONTROL OF STEREOCHEMISTRY IN THE SYNTHESIS OF 1-OXAQUINOLIZIDINE SKELETAL PORTIONS OF XESTOSPONGIN-A [J].

HOYE, TR ;

NORTH, JT .

TETRAHEDRON LETTERS, 1990, 31 (30) :4281-4284

[7] ATE COMPLEX FROM DIISOBUTYLALUMINUM HYDRIDE AND NORMAL-BUTYLLITHIUM AS A POWERFUL AND SELECTIVE REDUCING AGENT FOR THE REDUCTION OF SELECTED ORGANIC-COMPOUNDS CONTAINING VARIOUS FUNCTIONAL-GROUPS [J].

KIM, S ;

AHN, KH .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1717-1724

[8] ARAGUPETROSINE-A, A NEW VASODILATIVE MACROCYCLIC QUINOLIZIDINE ALKALOID FROM AN OKINAWAN MARINE SPONGE XESTOSPONGIA SP [J].

KOBAYASHI, M ;

KAWAZOE, K ;

KITAGAWA, I .

TETRAHEDRON LETTERS, 1989, 30 (31) :4149-4152

[9]

KOBAYASHI M, 1989, CHEM PHARM BULL, V37, P1676

[10] UNSATURATED AMINES .16. AN OXIDATIVE CYCLIZATION ROUTE TO OXAZOLIDINES AND TETRAHYDRO-1,3-OXAZINES [J].

LEONARD, NJ ;

MUSKER, WK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (19) :5148-5155

← 1 2 →