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Literature DB >> 23909645

Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.

Abstract

A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C.

Entities: Chemical Disease Species

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Year: 2013 PMID： 23909645 PMCID： PMC3788595 DOI： 10.1021/ol401954f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. 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

2. Stereocontrol of 1,5-related stereocentres using an intermediate silyl group--the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group.

Authors: Ian Fleming; Pranab Maiti; Chandrashekar Ramarao
Journal: Org Biomol Chem Date: 2003-11-21 Impact factor: 3.876

3. Substituent effects on the iodine-catalyzed thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates: mechanistic studies.

Authors: Ta-Hsien Chuang; Wei-Yu Chang; Chien-Fu Li; Yu-Chia Wen; Chia-Chen Tsai
Journal: J Org Chem Date: 2011-10-31 Impact factor: 4.354

4. Total synthesis of (-)-huperzine A.

Authors: Takahiro Koshiba; Satoshi Yokoshima; Tohru Fukuyama
Journal: Org Lett Date: 2009-11-19 Impact factor: 6.005

5. 1,2-migration in rhodium(II) carbene transfer reaction: remarkable steric effect on migratory aptitude.

Authors: Fengping Xiao; Jianbo Wang
Journal: J Org Chem Date: 2006-07-21 Impact factor: 4.354

6. Concise total synthesis of (+)-lyconadin A.

Authors: Takuya Nishimura; Aditya K Unni; Satoshi Yokoshima; Tohru Fukuyama
Journal: J Am Chem Soc Date: 2010-12-14 Impact factor: 15.419

7. Asymmetric total synthesis of (+)-luciduline: toward a general approach to related Lycopodium alkaloids.

Authors: Guillaume Barbe; Dominic Fiset; André B Charette
Journal: J Org Chem Date: 2011-06-01 Impact factor: 4.354

8. Construction of 5,6-Ring Fused 2-Pyridones: An Effective Annulation Tactic Achieved in Water.

Authors: Amos B Smith; Onur Atasoylu; Douglas C Beshore
Journal: Synlett Date: 2009-01-01 Impact factor: 2.454

9. Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline.

Authors: Xiayun Cheng; Stephen P Waters
Journal: Org Lett Date: 2010-01-15 Impact factor: 6.005

10. Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration.

Authors: Bradley L Nilsson; Larry E Overman; Javier Read de Alaniz; Jason M Rohde
Journal: J Am Chem Soc Date: 2008-08-02 Impact factor: 15.419

4 in total