Total Synthesis of (±)-Dysibetaine CPa and Analogs

被引：16

作者：

Oikawa, Masato ^{[1
,2
]}

Sasaki, Shota ^{[1
,2
]}

Sakai, Michihiro ^{[1
,2
]}

Ishikawa, Yuichi ^{[1
,2
]}

Sakai, Ryuichi ^{[3
]}

机构：

[1] Yokohama City Univ, Grad Sch Nanobiosci, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

[2] Yokohama City Univ, Univ Ind Cooperat Res Ctr, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

[3] Hokkaido Univ, Grad Sch Fisheries Sci, Hakodate, Hokkaido 0418611, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 29期

关键词：

Total synthesis; Natural products; Amino acids; Neurological agents; Diastereoselectivity; Chemoselectivity; EXCITATORY AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; NEODYSIHERBAINE-A; DYSIHERBAINE; DYSIBETAINE;

D O I：

10.1002/ejoc.201200730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of the marine sponge-derived ?-amino carboxylic acid dysibetaine CPa and five analogs in their racemic forms were successfully performed by taking advantage of an electron-withdrawing N-(4-nitrophenyl) group in the cyclopropanation reaction, the reductive ring opening of an imide, and the ethanolysis of an N-Boc-protected imide.

引用

页码：5789 / 5802

页数：14

共 33 条

[1] Highly enantioselective synthesis of chiral imides and derived products via chiral base desymmetrisation
Adams, DJ
Blake, AJ
Cooke, PA
Gill, CD
Simpkins, NS
[J]. TETRAHEDRON, 2002, 58 (23) : 4603 - 4615
[2] Catalytic cyclopropanation of electron deficient alkenes mediated by chiral and achiral sulfides: scope and limitations in reactions involving phenyldiazomethane and ethyl diazoacetate
Aggarwal, VK
Smith, HW
Hynd, G
Jones, RVH
Fieldhouse, R
Spey, SE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19): : 3267 - 3276
[3] An Expedient Asymmetric Synthesis of N-Protected (S,S)-2-Aminomethyl-1-cyclopropanecarboxylic Acid
Aitken, David J.
Bull, Steven D.
Davies, Iwan R.
Drouin, Ludovic
Ollivier, Jean
Peed, Jennifer
[J]. SYNLETT, 2010, (18) : 2729 - 2732
[4] Arai T., 1993, KAGAKU TO KYOIKU, V41, P278
[5] Synthesis and structure-activity relationship of N-(3-azabicyclo[3.1.0]hex-6-ylmethyl)-5-(2-pyridinyl)-1,3-thiazol-2-amines derivatives as NPY Y5 antagonists
Biagetti, Matteo
Leslie, Colin Philip
Mazzali, Angelica
Seri, Catia
Pizzi, Domenica Antonia
Bentley, Jonathan
Genski, Thorsten
Di Fabio, Romano
Zonzini, Laura
Caberlotto, Laura
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (16) : 4741 - 4744
[6] Improving the antiviral efficacy and selectivity of HIV-1 reverse transcriptase inhibitor TSAO-T by the introduction of functional groups at the N-3 position
Bonache, MC
Chamorro, C
Velázquez, S
De Clercq, E
Balzarini, J
Barrios, FR
Gago, F
Camarasa, MJ
San-Félix, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (21) : 6653 - 6660
[7] A concise asymmetric synthesis of (+)-muscarine from (S)-γ-hydroxymethyl-γ-butyrolactone
Boukouvalas, John
Radu, Ioan-Iosif
[J]. TETRAHEDRON LETTERS, 2007, 48 (17) : 2971 - 2973
[8] Ligands for glutamate receptors:: Design and therapeutic prospects
Bräuner-Osborne, H
Egebjerg, J
Nielsen, EO
Madsen, U
Krogsgaard-Larsen, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) : 2609 - 2645
[9] Cava M.P., 1961, ORG SYNTH, V41, P93
[10] Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides.: Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones
Coskun, N
Mert, H
Arikan, N
[J]. TETRAHEDRON, 2006, 62 (07) : 1351 - 1359

← 1 2 3 4 →