Model study for a general approach to morphine and noroxymorphone via a rare heck cyclization

被引：16

作者：

Frey, DA ^{[1
]}

Duan, CM ^{[1
]}

Hudlicky, T ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol991135g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.

引用

页码：2085 / 2087

页数：3

共 12 条

[1] Intramolecular N-acyliminium ion-olefin cyclization in the synthesis of optically pure isoquinoline derivatives: Control of stereochemistry and application to synthesis of morphine alkaloids [J].

Bottari, P ;

Endoma, MAA ;

Hudlicky, T ;

Ghiviriga, I ;

Abboud, KA .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (02) :203-216

[2]

Butora G, 1998, SYNTHESIS-STUTTGART, P665

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

Cheng, CY ;

Liou, JP ;

Lee, MJ .

TETRAHEDRON LETTERS, 1997, 38 (26) :4571-4574

[5] Studies into the direct oxidation of codeinone to 14-hydroxycodeinone [J].

Coop, A ;

Rice, KC .

TETRAHEDRON, 1999, 55 (38) :11429-11436

[6]

Crisp GT, 1998, CHEM SOC REV, V27, P427

[7] Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquinolines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations. [J].

Endoma, MA ;

Butora, G ;

Claeboe, CD ;

Hudlicky, T ;

Abboud, KA .

TETRAHEDRON LETTERS, 1997, 38 (51) :8833-8836

[8]

HECK RF, 1982, ORG REACTIONS, V27, P345

[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] CONVERGENT SYNTHESIS OF (+/-)-DIHYDROISOCODEINE IN 11 STEPS BY THE TANDEM RADICAL CYCLIZATION STRATEGY - A FORMAL TOTAL SYNTHESIS OF (+/-)-MORPHINE [J].

PARKER, KA ;

FOKAS, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9688-9689

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