Synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular Heck reaction

被引：23

作者：

Cheng, CY

Liou, JP

Lee, MJ

机构：

[1] Institute of Pharmaceutical Sciences, National Taiwan University, Taipei, 10018, 1, Sec 1, Jen-Ai Road

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(97)00976-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As a better alternative to radical cyclization, 5-(2-bromo-6-methoxyphenoxy)2-methyl-1,2,3,4,5,6,7,8- octahydroisoquinoline (2) and its 1-oxo analog 3 underwent Pd-catalyzed intramolecular cyclization to give the tetracyclic (ACNO) morphine fragments 5 and 6 respectively. 4-[(2'-Iodo-6'-methoxyphenoxy)methyl]-1-ethoxycarbonyl-1,2,5,6,- tetrahydropyridine (11) reacted similarly to provide the tricyclic ANO fragment 12 in 70% yield and 45% e.e. when a Pd-(S)-BINAP complex was used as the catalyst. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：4571 / 4574

页数：4

相关论文

共 20 条

[1]

[Anonymous], STUDIES NATURAL PROD

[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND [J].

ASHIMORI, A ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4571-4572

[3] Chemoenzymatic synthesis of the morphine skeleton via radical cyclization and a C-10-C-11 closure. [J].

Butora, G ;

Hudlicky, T ;

Fearnley, SP ;

Gum, AG ;

Stabile, MR ;

Abboud, K .

TETRAHEDRON LETTERS, 1996, 37 (45) :8155-8158

[4] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[5] SYNTHESIS AND OPIOID ACTIVITY OF 7-OXYGENATED 2,3,4,4A,5,6,7,7A-OCTAHYDRO-1H-BENZOFURO[3,2-E]ISOQUINOLIN-9-OLS [J].

CHENG, CY ;

HSIN, LW ;

TSAI, MC ;

SCHMIDT, WK ;

SMITH, C ;

TAM, SW .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (19) :3121-3127

[6] Novel radical synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline [J].

Cheng, CY ;

Hsin, LW ;

Liou, JP .

TETRAHEDRON, 1996, 52 (33) :10935-10944

[7] THE SYNTHESIS OF MORPHINE [J].

GATES, M ;

TSCHUDI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (04) :1109-1110

[8] PREPARATION OF OPIUM-ALKALOIDS BY PALLADIUM-CATALYZED BIS-CYCLIZATIONS - FORMAL TOTAL SYNTHESIS OF MORPHINE [J].

HONG, CY ;

OVERMAN, LE .

TETRAHEDRON LETTERS, 1994, 35 (21) :3453-3456

[9] ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF OPIUM-ALKALOIDS AND MORPHINANS - TOTAL SYNTHESIS OF (-)-DIHYDROCODEINONE AND (+)-DIHYDROCODEINONE AND (-)-MORPHINE AND (+)-MORPHINE [J].

HONG, CY ;

KADO, N ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11028-11029

[10] Total syntheses of vincadifformine, 3-oxovincadifformine, pseudo- and 20-epi-pseudovincadifformine, tabersonine, and Delta(18)-tabersonine through radical reactions and Heck reaction [J].

Kuehne, ME ;

Wang, TS ;

Seaton, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :6001-6008