环色胺生物碱霍奇金碱和霍奇金碱B的对映选择性全合成。 - Suppr

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Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B.

作者信息

Kodanko Jeremy J, Overman Larry E

机构信息

Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, CA 92697-2025, USA.

出版信息

Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2528-31. doi: 10.1002/anie.200351261.

DOI:10.1002/anie.200351261

PMID:12800178

Abstract

摘要

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Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B.

作者信息

Kodanko Jeremy J, Overman Larry E

机构信息

Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, CA 92697-2025, USA.

出版信息

Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2528-31. doi: 10.1002/anie.200351261.

DOI:10.1002/anie.200351261

PMID:12800178

Abstract

摘要

相似文献

Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B.

Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2528-31. doi: 10.1002/anie.200351261.

Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity.

J Org Chem. 2007 Oct 12;72(21):7909-14. doi: 10.1021/jo7013643. Epub 2007 Sep 21.

Enantioselective total syntheses of (+)-arborescidine A, (-)-arborescidine B, and (-)-arborescidine C.

J Org Chem. 2004 Feb 20;69(4):1283-9. doi: 10.1021/jo035165f.

Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G.

J Am Chem Soc. 2005 Nov 9;127(44):15394-6. doi: 10.1021/ja056171r.

Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B.

Chemistry. 2012 Dec 21;18(52):16754-64. doi: 10.1002/chem.201203150. Epub 2012 Nov 30.

Enantiospecific, stereospecific total synthesis of the oxindole alkaloid alstonisine.

Org Lett. 2002 Nov 28;4(24):4237-40. doi: 10.1021/ol020170b.

A short total synthesis of (+/-)-aspidospermidine.

Org Lett. 2006 Mar 2;8(5):831-4. doi: 10.1021/ol052749q.

Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline.

Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2525-8. doi: 10.1002/anie.200351260.

Concise synthesis of the (+/-)-Nb-desmethyl-meso-chimonanthine.

Chem Commun (Camb). 2006 Nov 28(44):4638-40. doi: 10.1039/b610497e. Epub 2006 Oct 3.

Enantiospecific synthesis of (+)-alstonisine via a stereospecific osmylation process.

J Nat Prod. 2008 Aug;71(8):1431-40. doi: 10.1021/np800269k. Epub 2008 Jul 9.

引用本文的文献

Unified, Biosynthesis-Inspired, Completely Stereocontrolled Total Synthesis of All Highest-Order [n + 1] Oligocyclotryptamine Alkaloids.

J Am Chem Soc. 2024 Aug 21;146(33):23574-23581. doi: 10.1021/jacs.4c07705. Epub 2024 Aug 12.

Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling.

Chem Sci. 2024 Jan 4;15(6):2205-2210. doi: 10.1039/d3sc05210a. eCollection 2024 Feb 7.

Total Synthesis and Stereochemical Assignment of (-)-Psychotridine.

Org Lett. 2022 Mar 25;24(11):2160-2164. doi: 10.1021/acs.orglett.2c00448. Epub 2022 Mar 17.

Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold.

J Am Chem Soc. 2020 Jul 8;142(27):11685-11690. doi: 10.1021/jacs.0c04760. Epub 2020 Jun 23.

Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.

J Am Chem Soc. 2018 Mar 7;140(9):3394-3402. doi: 10.1021/jacs.7b13616. Epub 2018 Feb 21.

Catalyst-controlled oligomerization for the collective synthesis of polypyrroloindoline natural products.

Nat Chem. 2017 Dec;9(12):1165-1169. doi: 10.1038/nchem.2825. Epub 2017 Jul 24.

Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.

J Am Chem Soc. 2017 Dec 6;139(48):17590-17596. doi: 10.1021/jacs.7b09929. Epub 2017 Nov 20.

Total Synthesis of Dimeric HPI Alkaloids.

Nat Prod Bioprospect. 2016 Apr;6(2):117-39. doi: 10.1007/s13659-016-0092-8. Epub 2016 Mar 11.

Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

J Am Chem Soc. 2016 Jan 27;138(3):1057-64. doi: 10.1021/jacs.5b12392. Epub 2016 Jan 19.

Stereocontrolled enantioselective total synthesis of the [2+2] quadrigemine alkaloids.

Tetrahedron. 2015 Sep 16;71(37):6424-6436. doi: 10.1016/j.tet.2015.02.080.