Synthesis of sedamine by tethered cyclofunctionalisation

被引：23

作者：

Bates, RW

Boonsombat, J

机构：

[1] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

[2] Chulabhorn Res Inst, Med Chem Lab, Bangkok 10210, Thailand

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 03期

关键词：

D O I：

10.1039/b415297b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The piperidine alkaloid, (+)-sedamine has been synthesised starting from (S)-1-phenyl-3-butenol using a stereoselective, intramolecular palladium-catalysed cyclocarbonylation reaction of a substituted hydroxylamine.

引用

页码：520 / 523

页数：4

共 15 条

[1] Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine
Angoli, M
Barilli, A
Lesma, G
Passarella, D
Riva, S
Silvani, A
Danieli, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9525 - 9527
[2] Syntheses of the sedum and related alkaloids
Bates, RW
Sa-Ei, K
[J]. TETRAHEDRON, 2002, 58 (30) : 5957 - 5978
[3] O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization
Bates, RW
Sa-Ei, K
[J]. ORGANIC LETTERS, 2002, 4 (24) : 4225 - 4227
[4] THE ADDITION OF METALLO-ENOLATES TO CHIRAL 1-ACYLPYRIDINIUM SALTS - AN ASYMMETRIC-SYNTHESIS OF (-)-SEDAMINE
COMINS, DL
HONG, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) : 5035 - 5036
[5] Enantioselective allyltitanations and metathesis reactions. application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline
Cossy, J
Willis, C
Bellosta, V
BouzBouz, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) : 1982 - 1992
[6] EFFECT OF AMINES ON O-BENZYL GROUP HYDROGENOLYSIS
CZECH, BP
BARTSCH, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 4076 - 4078
[7] A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine
Felpin, FX
Lebreton, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) : 9192 - 9199
[8] A user-friendly entry to 2-iodoxybenzoic acid (IBX)
Frigerio, M
Santagostino, M
Sputore, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) : 4537 - 4538
[9] Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid:: Application to catalytic asymmetric allylation of aldehydes
Hanawa, H
Hashimoto, T
Maruoka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) : 1708 - 1709
[10] Meth CO, 2000, Eur Pat., Patent No. [1050531, 1,050,531]

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