Synthetic studies on lycopodium alkaloid, magellanine: Stereoselective construction of functionallized angular tricyclic skeletons by intramolecular Pauson-Khand reaction

被引：17

作者：

Ishizaki, M ^{[1
]}

Niimi, Y ^{[1
]}

Hoshino, O ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Shinjuku Ku, Tokyo 1620826, Japan

来源：

CHEMISTRY LETTERS | 2001年 / 06期

关键词：

D O I：

10.1246/cl.2001.546

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Angular tricyclic compounds as intermediates for total synthesis of magellanine were synthesized by stereoselective Ireland-Claisen rearrangement and intramolecular Pauson-Khand reaction of exo-methylenecyclohexylalkynes. Interestingly, remarkably different reactivity was observed in the Pauson-Khand reaction of cis- and trans-disubstituted exo-methylenecyclohexylalkynes.

引用

页码：546 / 547

页数：2

共 14 条

[1]

[Anonymous], ALDRICHIMICA ACTA

[2] Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].

Brummond, KM ;

Kent, JL .

TETRAHEDRON, 2000, 56 (21) :3263-3283

[3] ALKALOIDS OF L-MAGELLANICUM AND STRUCTURE OF MAGELLANINE [J].

CASTILLO, M ;

LOYOLA, LA ;

MORALES, G ;

SINGH, I ;

CALVO, C ;

HOLLAND, HL ;

MACLEAN, DB .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (18) :2893-2899

[4] 1ST TOTAL SYNTHESIS OF LYCOPODIUM ALKALOIDS OF THE MAGELLANANE GROUP - ENANTIOSELECTIVE TOTAL SYNTHESES OF (-)-MAGELLANINE AND (+)-MAGELLANINONE [J].

HIRST, GC ;

JOHNSON, TO ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2992-2993

[5]

Ishizaki M, 1999, SYNLETT, P587

[6] Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson-Khand reaction of exo- and endo-cyclic enynes [J].

Ishizaki, M ;

Iwahara, K ;

Niimi, Y ;

Satoh, H ;

Hoshino, O .

TETRAHEDRON, 2001, 57 (14) :2729-2738

[7] LANTHANOIDS IN ORGANIC-SYNTHESIS .5. SELECTIVE REDUCTIONS OF KETONES IN THE PRESENCE OF ALDEHYDES [J].

LUCHE, JL ;

GEMAL, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) :5848-5849

[8] Synthetic studies towards novel tetracyclic Lycopodium alkaloids: A synthesis of deoxymagellaninone [J].

Mehta, G ;

Reddy, MS ;

Thomas, A .

TETRAHEDRON, 1998, 54 (27) :7865-7882

[9] DICHLOROKETENE-OLEFIN CYCLOADDUCTS IN SYNTHESIS - A SHORT, CONVENIENT, PROTOCOL FOR OLEFIN-]ALPHA-VINYLKETONE TRANSFORMATION [J].

MEHTA, G ;

ACHARYULU, PVR .

TETRAHEDRON LETTERS, 1993, 34 (50) :8157-8158

[10] TOTAL SYNTHESIS OF THE TETRACYCLIC DIQUINANE LYCOPODIUM ALKALOIDS MAGELLANINE AND MAGELLANINONE [J].

PAQUETTE, LA ;

FRIEDRICH, D ;

PINARD, E ;

WILLIAMS, JP ;

STLAURENT, D ;

RODEN, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4377-4378

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