Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer

被引：114

作者：

Davis, FA ^{[1
]}

Chao, B ^{[1
]}

Rao, A ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol0164839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS The intramolecular Mannich reaction of delta -amino beta -keto esters with aldehydes and ketones is a new methodology for the synthesis of polysubstituted piperidines and is illustrated by the concise asymmetric synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer.

引用

收藏

页码：3169 / 3171

页数：3

相关论文

共 19 条

[1] STUDIES ON CONFORMATION .1. PREPARATION AND STEREOCHEMISTRY OF SOME 4-PIPERIDINOLS [J].

BALASUBRAMANIAN, M ;

PADMA, N .

TETRAHEDRON, 1963, 19 (12) :2135-&

[2] Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D [J].

Chenevert, R ;

Dickman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3332-3341

[3] A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines [J].

Ciblat, S ;

Besse, P ;

Canet, JL ;

Troin, Y ;

Veschambre, H ;

Gelas, J .

TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2225-2235

[4] A simple synthesis of (+)- and (-)-alkaloid 241D and C-4 epimers [J].

Ciblat, S ;

Calinaud, P ;

Canet, JL ;

Troin, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :353-357

[5]

Davis FA, 2000, SYNTHESIS-STUTTGART, P2106

[6] δ-amino β-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis.: Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A [J].

Davis, FA ;

Chao, B ;

Fang, TN ;

Szewczyk, JM .

ORGANIC LETTERS, 2000, 2 (08) :1041-1043

[7] Alkaloid synthesis using chiral δ-amino β-ketoesters:: A stereoselective synthesis of (-)-lasubine II [J].

Davis, FA ;

Chao, B .

ORGANIC LETTERS, 2000, 2 (17) :2623-2625

[8]

Davis FA, 1998, CHEM SOC REV, V27, P13

[9] Introduction (Audience research in the theatre) [J].

Davis, TC ;

Mcconachie, B .

THEATRE SURVEY, 1998, 39 (02) :1-5

[10] ALKALOIDS FROM A PANAMANIAN POISON FROG, DENDROBATES-SPECIOSUS - IDENTIFICATION OF PUMILIOTOXIN-A AND ALLOPUMILIOTOXIN CLASS ALKALOIDS, 3,5-DISUBSTITUTED INDOLIZIDINES, 5-SUBSTITUTED 8-METHYLINDOLIZIDINES, AND A 2-METHYL-6-NONYL-4-HYDROXYPIPERIDINE [J].

EDWARDS, MW ;

DALY, JW .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (06) :1188-1197