加纳尔醛作为一种多功能中间体，在合成手性纯天然产物中的应用。
Garner's aldehyde as a versatile intermediate in the synthesis of enantiopure natural products.
机构信息
Aalto-University, School of Chemical Technology, Department of Chemistry P.O. Box 16100 (Kemistintie 1), FI-00076 Aalto, Finland.
出版信息
Beilstein J Org Chem. 2013 Nov 26;9:2641-59. doi: 10.3762/bjoc.9.300.
Abstract
Since its introduction to the synthetic community in 1984, Garner's aldehyde has gained substantial attention as a chiral intermediate for the synthesis of numerous amino alcohol derivatives. This review presents some of the most successful carbon chain elongation reactions, namely carbonyl alkylations and olefinations. The literature is reviewed with particular attention on understanding how to avoid the deleterious epimerization of the existing stereocenter in Garner's aldehyde.
摘要
自 1984 年引入合成领域以来，Garner 醛作为合成众多氨基醇衍生物的手性中间体，受到了广泛关注。本文综述了一些最成功的碳链延长反应，即羰基烷基化和烯烃化反应。本文特别关注如何避免 Garner 醛中现有手性中心的有害差向异构化，对文献进行了综述。
相似文献
1
Garner's aldehyde as a versatile intermediate in the synthesis of enantiopure natural products.
Beilstein J Org Chem. 2013 Nov 26;9:2641-59. doi: 10.3762/bjoc.9.300.
2
Highly efficient and enantioselective syntheses of (2S,3R)-3-alkyl- and alkenylglutamates from Fmoc-protected Garner's aldehyde.
Amino Acids. 2020 Jul;52(6-7):987-998. doi: 10.1007/s00726-020-02868-7. Epub 2020 Jul 3.
3
Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate.
Beilstein J Org Chem. 2017 Jan 17;13:106-110. doi: 10.3762/bjoc.13.13. eCollection 2017.
4
Stereoselective Synthesis of (4,5)-5-Vinyloxazolidin-2-one-4-carboxylate as a β-Vinylserine Synthetic Equivalent by Vinyl Grignard Addition to an -Tosyl Version of Garner's Aldehyde.
Synlett. 2021;32(6):601-604. doi: 10.1055/a-1308-0370. Epub 2020 Nov 10.
5
Enantioselective synthesis of Garner's aldehyde by asymmetric hydroformylation.
J Org Chem. 2012 Mar 16;77(6):2983-5. doi: 10.1021/jo300025t. Epub 2012 Mar 7.
6
Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner's aldehyde as versatile building blocks.
Bioorg Med Chem Lett. 2021 May 15;40:127961. doi: 10.1016/j.bmcl.2021.127961. Epub 2021 Mar 17.
7
Ethynylglycine synthon from Garner's aldehyde: a useful precursor for the synthesis of non-natural amino acids.
Amino Acids. 2005 Aug;29(2):81-7. doi: 10.1007/s00726-005-0184-y. Epub 2005 Apr 11.
8
Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds.
Org Lett. 2004 Sep 2;6(18):3171-4. doi: 10.1021/ol0487433.
9
-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds.
Beilstein J Org Chem. 2019 Jul 23;15:1722-1757. doi: 10.3762/bjoc.15.168. eCollection 2019.
10
An efficient enantioselective synthesis of (2R)-hydroxymethyl glutamic acid and an approach to the (2R)-hydroxymethyl-substituted sphingofungins.
J Org Chem. 2006 Mar 31;71(7):2661-5. doi: 10.1021/jo052408q.
引用本文的文献
1
A Decarbonylative Strategy to Enhance Efficiency and Regioselectivity in Photocatalyzed Hydrogen Atom Transfer.
JACS Au. 2025 Jun 16;5(7):3491-3499. doi: 10.1021/jacsau.5c00530. eCollection 2025 Jul 28.
2
Stereoselective amino alcohol synthesis via chemoselective electrocatalytic radical cross-couplings.
Nat Chem. 2025 Jan;17(1):44-53. doi: 10.1038/s41557-024-01695-7. Epub 2025 Jan 3.
3
The operon is a marker of C4-alkylated monobactam biosynthesis and responsible for (,)-diaminobutyrate production.
iScience. 2024 Feb 12;27(3):109202. doi: 10.1016/j.isci.2024.109202. eCollection 2024 Mar 15.
4
Dipeptide-Derived Alkynes as Potent and Selective Irreversible Inhibitors of Cysteine Cathepsins.
J Med Chem. 2023 Mar 23;66(6):3818-3851. doi: 10.1021/acs.jmedchem.2c01360. Epub 2023 Mar 3.
5
Process Engineering and Glycosyltransferase Improvement for Short Route Chemoenzymatic Total Synthesis of GM1 Gangliosides.
Chemistry. 2023 May 2;29(25):e202300005. doi: 10.1002/chem.202300005. Epub 2023 Mar 17.
6
Synthetic Thiol and Selenol Derived Amino Acids for Expanding the Scope of Chemical Protein Synthesis.
Front Chem. 2022 Feb 14;9:826764. doi: 10.3389/fchem.2021.826764. eCollection 2021.
7
Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis.
Chemistry. 2022 Feb 7;28(8):e202103883. doi: 10.1002/chem.202103883. Epub 2021 Dec 28.
8
Stereoselective Synthesis of (4,5)-5-Vinyloxazolidin-2-one-4-carboxylate as a β-Vinylserine Synthetic Equivalent by Vinyl Grignard Addition to an -Tosyl Version of Garner's Aldehyde.
Synlett. 2021;32(6):601-604. doi: 10.1055/a-1308-0370. Epub 2020 Nov 10.
9
-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds.
Beilstein J Org Chem. 2019 Jul 23;15:1722-1757. doi: 10.3762/bjoc.15.168. eCollection 2019.
10
Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks.
Org Lett. 2018 Jun 15;20(12):3574-3578. doi: 10.1021/acs.orglett.8b01358. Epub 2018 Jun 1.
本文引用的文献
1
A new class of antitumor compounds: 5'-nor and 5',6'-seco derivatives of vinblastine-type alkaloids.
J Org Chem. 1979 Oct 1;44(22):3765-8. doi: 10.1021/jo01336a006.
2
Total synthesis and structural revision of lucentamycin A.
J Org Chem. 2012 Nov 2;77(21):9859-64. doi: 10.1021/jo301723y. Epub 2012 Oct 16.
3
A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates.
Tetrahedron Asymmetry. 2006 Nov 27;17(22):3170-3176. doi: 10.1016/j.tetasy.2006.11.029.
4
Diastereoselective synthesis of vicinal amino alcohols.
Org Biomol Chem. 2012 Jun 14;10(22):4311-26. doi: 10.1039/c2ob25357g. Epub 2012 Apr 25.
5
Enantioselective synthesis of Garner's aldehyde by asymmetric hydroformylation.
J Org Chem. 2012 Mar 16;77(6):2983-5. doi: 10.1021/jo300025t. Epub 2012 Mar 7.
6
Practical syntheses of proposed and revised manzacidin B and their congeners.
Org Lett. 2012 Feb 17;14(4):1082-5. doi: 10.1021/ol203466m. Epub 2012 Feb 8.
7
Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates.
Org Biomol Chem. 2011 Mar 21;9(6):1774-83. doi: 10.1039/c0ob00643b. Epub 2011 Jan 24.
8
Rapid and practical synthesis of (-)-1-deoxyaltronojirimycin.
Org Biomol Chem. 2011 Feb 21;9(4):1231-6. doi: 10.1039/c0ob00747a. Epub 2010 Dec 24.
9
Diastereoselective Nickel-Catalyzed Reductive Couplings of Aminoaldehydes and Alkynylsilanes: Application to the Synthesis of D-erythro-Sphingosine.
Tetrahedron. 2009 Sep 15;65(33):6707-6711. doi: 10.1016/j.tet.2009.05.029.
10
Short and straightforward synthesis of (-)-1-deoxygalactonojirimycin.
Org Lett. 2010 Mar 19;12(6):1145-7. doi: 10.1021/ol100037c.
Zotero 插件