Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo-[3,2-a]pyridin-4-ylium bromide:: Synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine

被引：18

作者：

Castro, Alejandro ^{[1
]}

Ramirez, Johana ^{[1
]}

Juarez, Jorge ^{[1
]}

Teran, Joel L. ^{[1
]}

Orea, Laura ^{[1
]}

Galindo, Alberto ^{[1
]}

Gnecco, Dino ^{[1
]}

机构：

[1] Ctr Chem, Inst Sci, Synth Organ Lab, BUAP, Puebla, Mexico

来源：

HETEROCYCLES | 2007年 / 71卷 / 12期

关键词：

hexahydrooxazolo[3,2-a]pyridin-4-ylium bromide; phosphorus oxybromide; reduction; phenylhexahydrooxazolo[3,2-a]pyridine;

D O I：

10.1016/S0385-5414(07)81205-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3, Reduction of 2 with Red-Al at -78 degrees C gave (3R,8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.

引用

页码：2699 / 2708

页数：10

共 30 条

[1] Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A [J].

Amat, M ;

Hidalgo, J ;

Llor, N ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2419-2422

[2] Dynamic kinetic resolution and desymmetrization processes:: A straightforward methodology for the enantioselective synthesis of piperidines [J].

Amat, Mercedes ;

Bassas, Oriol ;

Llor, Nuria ;

Canto, Margalida ;

Perez, Maria ;

Molins, Elies ;

Bosch, Joan .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) :7872-7881

[3]

Angle S. R., 1995, STUD NAT PROD CHEM, V16, P453

[4]

[Anonymous], 1993, ALKALOIDS CHEM PHARM

[5]

[Anonymous], 1985, ALKALOIDS CHEM BIOL

[6] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[7] Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones [J].

Comins, DL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) :1491-1500

[8]

Daly JW., 1986, ALKALOIDS CHEM BIOL, P1

[9] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[10]

FEVILLE S, 1997, TETRAHEDRON, V53, P8447

← 1 2 3 →