Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine

被引：55

作者：

Bower, JF

Szeto, P

Gallagher, T

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] GlaxoSmithKline Inc, Chem Dev, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 46期

关键词：

D O I：

10.1039/b510761j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short and efficient enantioselective synthesis of (-)-aphanorphine is described based on the use of a cyclic sulfamidate to provide a suitably functionalised lactam that allows for construction of the tricyclic 3-benzazepine scaffold.

引用

页码：5793 / 5795

页数：3

共 30 条

[1] THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN [J].

ALKER, D ;

DOYLE, KJ ;

HARWOOD, LM ;

MCGREGOR, A .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :877-880

[2] Cyclic sulfamidates as vehicles for the synthesis of substituted lactams [J].

Bower, JF ;

Svenda, J ;

Williams, AJ ;

Charmant, JPH ;

Lawrence, RM ;

Szeto, P ;

Gallagher, T .

ORGANIC LETTERS, 2004, 6 (25) :4727-4730

[3] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[4]

El-Azab AS, 2002, HETEROCYCLES, V56, P39

[5] Enzymatic asymmetrisation of prochiral alpha,alpha-disubstituted-malonates and -1,3-propanediols: Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine [J].

Fadel, A ;

Arzel, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :371-374

[6] ASYMMETRIC CONSTRUCTION OF BENZYLIC QUATERNARY CARBONS FROM CHIRAL MALONATES - FORMAL SYNTHESIS OF NATURAL (-)APHANORPHINE [J].

FADEL, A ;

ARZEL, P .

TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :893-900

[7] Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins [J].

Fuchs, JR ;

Funk, RL .

ORGANIC LETTERS, 2001, 3 (24) :3923-3925

[8] APHANORPHINE, A NOVEL TRICYCLIC ALKALOID FROM THE BLUE-GREEN-ALGA APHANIZOMENON-FLOS-AQUAE [J].

GULAVITA, N ;

HORI, A ;

SHIMIZU, Y ;

LASZLO, P ;

CLARDY, J .

TETRAHEDRON LETTERS, 1988, 29 (35) :4381-4384

[9]

HALLINAN KO, 1995, TETRAHEDRON, V51, P12211

[10] SYNTHESIS OF (+/-)-APHANORPHINE VIA AN AMINYLIUM ION INTERMEDIATE [J].

HONDA, T ;

YAMAMOTO, A ;

CUI, YS ;

TSUBUKI, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :531-532

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