Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine

被引：36

作者：

Bates, Roderick W. ^{[1
]}

Nemeth, Joseph A. ^{[1
]}

Snell, Robert H. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Math & Phys Sci, Singapore 637371, Singapore

来源：

SYNTHESIS-STUTTGART | 2008年 / 07期

关键词：

cyclisation; allenes; heterocycles; alkaloids; stereoselectivity;

D O I：

10.1055/s-2008-1066985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.

引用

页码：1033 / 1038

页数：6

共 38 条

[1]

Amombo MO, 1999, SYNLETT, P1871

[2] Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine [J].

Angoli, M ;

Barilli, A ;

Lesma, G ;

Passarella, D ;

Riva, S ;

Silvani, A ;

Danieli, B .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9525-9527

[3] Recent applications of gold catalysis in organic synthesis [J].

Arcadi, A ;

Di Giuseppe, S .

CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812

[4] CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES [J].

ARSENIYADIS, S ;

GORE, J .

TETRAHEDRON LETTERS, 1983, 24 (37) :3997-4000

[5] AN EFFICIENT SYNTHESIS OF (+/-)-PINIDINE [J].

ARSENIYADIS, S ;

SARTORETTI, J .

TETRAHEDRON LETTERS, 1985, 26 (06) :729-732

[6] Syntheses of the sedum and related alkaloids [J].

Bates, RW ;

Sa-Ei, K .

TETRAHEDRON, 2002, 58 (30) :5957-5978

[7] O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization [J].

Bates, RW ;

Sa-Ei, K .

ORGANIC LETTERS, 2002, 4 (24) :4225-4227

[8] Nucleophilic transition metal based cyclization of allenes [J].

Bates, RW ;

Satcharoen, V .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21

[9] Stereoselective total synthesis of (+)-sedamine [J].

Borah, JC ;

Boruwa, J ;

Barua, NC .

LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (02) :140-142

[10]

BRANDSMA L, 1988, PREPARATIVE ACETYLEN, P67

← 1 2 3 4 →