Asymmetric synthesis of (-)-nupharamine and (-)-(5S, 8R, 9S)-5-(3-furyl)-8-methyloctahydroindolizidine from β-amino ketones and the intramolecular Mannich reaction

被引：40

作者：

Davis, Franklin A. ^{[1
]}

Santhanaraman, Manikandan ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 11期

关键词：

D O I：

10.1021/jo060371j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of the 2,3,6-trisubstituted piperidine core of the antitumor Nuphar alkaloids was readily achieved by using the intramolecular Mannich reaction and a sulfinimine-derived beta-amino ketone.

引用

页码：4222 / 4226

页数：5

共 34 条

[21] A CONCISE ENANTIOSPECIFIC SYNTHESIS OF NUPHAR PIPERIDINE ALKALOIDS - TOTAL SYNTHESIS OF (-)-ANHYDRONUPHARAMINE, (-)-NUPHARAMINE, (-)-NUPHENINE AND (+)-3-EPINUPHARAMINE [J].

HONDA, T ;

ISHIKAWA, F ;

YAMANE, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) :499-500

[22]

Kokate M., 1962, B CHEM SOC JPN, V35, P698

[23] DIMER ALKALOID OF 6,7 BETA-OXIDODEOXYNUPHARIDINE [J].

LALONDE, RT ;

WONG, CF ;

DAS, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (24) :8522-&

[24]

MATSUA H, 2003, BIOORG MED CHEM LETT, V16, P1567

[25] Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum [J].

Matsuda, H ;

Morikawa, T ;

Oda, M ;

Asao, Y ;

Yoshikawa, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (24) :4445-4449

[26] Dimeric sesquiterpene thioalkaloids with potent immunosuppressive activity from the rhizome of Nuphar pumilum:: Structural requirements of Nuphar alkaloids for immunosuppressive activity [J].

Matsuda, H ;

Shimoda, H ;

Yoshikawa, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (04) :1031-1035

[27] INVESTIGATION OF NITROGEN-CONTAINING COMPOUNDS OF CASTOREUM [J].

MAURER, B ;

OHLOFF, G .

HELVETICA CHIMICA ACTA, 1976, 59 (04) :1169-1185

[28] Indolizidine and quinolizidine alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 2005, 22 (05) :603-626

[29] Indolizidine and quinolizidine alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 1999, 16 (06) :675-696

[30] CHIRAL SYNTHESIS OF (-)-NUPHARAMINE [J].

SHIMIZU, I ;

YAMAZAKI, H .

CHEMISTRY LETTERS, 1990, (05) :777-778

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