Syntheses of (+)-cytisine, (-)-kuraramine, (-)-isokuraramine, and (-)-jussiaefine A

被引：72

作者：

Honda, T ^{[1
]}

Takahashi, R ^{[1
]}

Namiki, H ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo048365f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DIAGRAM Total syntheses of (+)-cytisine, (-)-kuraramine.. (-)-isokuraramine, and (-)-jussiaeiine A were achieved via a samarium diiodide-promoted reductive deamination reaction. followed by simultaneous recyclization of a proline derivative to give the corresponding delta-lactam derivative, as a key step.

引用

页码：499 / 504

页数：6

共 36 条

[1] An efficient enantioselective synthesis of (S)-(-)-acromelobic acid
Adamczyk, M
Akireddy, SR
Reddy, RE
[J]. ORGANIC LETTERS, 2000, 2 (22) : 3421 - 3423
[2] Total synthesis of pyridovericin: Studies toward the biomimetic synthesis of pyridomacrolidin
Baldwin, JE
Adlington, RM
Conte, A
Irlapati, NR
Marquez, R
Pritchard, GJ
[J]. ORGANIC LETTERS, 2002, 4 (13) : 2125 - 2127
[3] SOME STUDIES ON CYTISINE AND ITS METHYLATED DERIVATIVES
BARLOW, RB
MCLEOD, LJ
[J]. BRITISH JOURNAL OF PHARMACOLOGY, 1969, 35 (01) : 161 - &
[4] BOHLMANN F, 1956, CHEM BER-RECL, V89, P792
[5] A short synthesis of (±)-cytisine
Botuha, C
Galley, CMS
Gallagher, T
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (13) : 1825 - 1826
[6] Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides
Coe, JW
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4205 - 4208
[7] Total enantioselective synthesis of (-)-cytisine
Danieli, B
Lesma, G
Passarella, D
Sacchetti, A
Silvani, A
Virdis, A
[J]. ORGANIC LETTERS, 2004, 6 (04) : 493 - 496
[8] ElShazly A, 1996, PHARMAZIE, V51, P768
[9] Synthesis of phenanthridones, quinolinequinones and 7-azasteroids
González, C
Guitián, E
Castedo, L
[J]. TETRAHEDRON, 1999, 55 (16) : 5195 - 5206
[10] SYNTHESIS OF (+/-)-CYTISINE
GOVINDACHARI, TR
RAJADURAI, S
SUBRAMANIAN, M
THYAGARAJAN, BS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (SEP): : 3839 - 3844

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