Literature DB >> 24596132

Divergent total syntheses of lyconadins A and C.

Yang Yang1, Christopher W Haskins, Wandi Zhang, Pui Leng Low, Mingji Dai.   

Abstract

Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; cyclizations; drug discovery; natural products; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 24596132      PMCID： PMC4113559          DOI： 10.1002/anie.201400416

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  37 in total

Review 1.  Neuronal cell death, nerve growth factor and neurotrophic models: 50 years on.

Authors:  M R Bennet; W G Gibson; G Lemon
Journal:  Auton Neurosci       Date:  2002-01-10       Impact factor: 3.145

2.  Lyconadin A, a novel alkaloid from Lycopodium complanatum.

Authors:  J Kobayashi; Y Hirasawa; N Yoshida; H Morita
Journal:  J Org Chem       Date:  2001-08-24       Impact factor: 4.354

Review 3.  Localized striatal delivery of GDNF as a treatment for Parkinson disease.

Authors:  Deniz Kirik; Biljana Georgievska; Anders Björklund
Journal:  Nat Neurosci       Date:  2004-01-27       Impact factor: 24.884

4.  Highly efficient synthesis of terminal alkenes from ketones.

Authors:  Hélène Lebel; Danielle Guay; Valérie Paquet; Kim Huard
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

5.  Direct catalytic enantioselective aza-Diels-Alder reactions.

Authors:  Henrik Sundén; Ismail Ibrahem; Lars Eriksson; Armando Córdova
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-05       Impact factor: 15.336

Review 6.  Nerve growth factor signaling, neuroprotection, and neural repair.

Authors:  M V Sofroniew; C L Howe; W C Mobley
Journal:  Annu Rev Neurosci       Date:  2001       Impact factor: 12.449

Review 7.  The Lycopodium alkaloids.

Authors:  Xiaoqiang Ma; David R Gang
Journal:  Nat Prod Rep       Date:  2004-10-21       Impact factor: 13.423

8.  Generation and trapping of alkene radical cations under nonoxidizing conditions: formation of six-membered rings by exo- and endo-mode cyclizations.

Authors:  David Crich; Santhosh Neelamkavil
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005

Review 9.  Neurotrophins and neurodegeneration.

Authors:  D Dawbarn; S J Allen
Journal:  Neuropathol Appl Neurobiol       Date:  2003-06       Impact factor: 8.090

10.  Structure of nerve growth factor complexed with the shared neurotrophin receptor p75.

Authors:  Xiao-Lin He; K Christopher Garcia
Journal:  Science       Date:  2004-05-07       Impact factor: 47.728
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  3 in total

1.  Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile.

Authors:  Wandi Zhang; Christopher W Haskins; Yang Yang; Mingji Dai
Journal:  Org Biomol Chem       Date:  2014-12-07       Impact factor: 3.876

2.  Total Syntheses of Lyconadins: Finding Efficiency and Diversity.

Authors:  Yang Yang; Mingji Dai
Journal:  Synlett       Date:  2014       Impact factor: 2.454

3.  Concise synthesis of (+)-fastigiatine.

Authors:  Renzo A Samame; Christina M Owens; Scott D Rychnovsky
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825
  3 in total

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