Literature DB >> 10822560

IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: asymmetric synthesis of (+)-luciduline.

D L Comins1, C A Brooks, R S al-awar, R R Goehring.   

Abstract

[formula: see text] The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich ring opening, and a novel cationic reductive cyclization reaction.

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Year:  1999        PMID： 10822560     DOI： 10.1021/ol990028j

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


  9 in total

1.  Asymmetric synthesis of all the known phlegmarine alkaloids.

Authors:  Bradley H Wolfe; Adam H Libby; Rima S Al-Awar; Christopher J Foti; Daniel L Comins
Journal:  J Org Chem       Date:  2010-11-15       Impact factor: 4.354

Review 2.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

3.  Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

Authors:  Hua Yang; Rich G Carter
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

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

Authors:  Xiayun Cheng; Stephen P Waters
Journal:  Org Lett       Date:  2013-08-02       Impact factor: 6.005

5.  Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2013-01-15       Impact factor: 6.005

6.  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

7.  Studies toward the total synthesis of dihydrolycolucine. Preparation of AB and CEF ring fragments.

Authors:  Brandon M Cash; Natacha Prevost; Florence F Wagner; Daniel L Comins
Journal:  J Org Chem       Date:  2014-05-29       Impact factor: 4.354

8.  Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors.

Authors:  Yafei Guo; Syuzanna R Harutyunyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

9.  Rh2(II)-catalyzed selective aminomethylene migration from styryl azides.

Authors:  Chen Kong; Navendu Jana; Tom G Driver
Journal:  Org Lett       Date:  2013-02-04       Impact factor: 6.005
  9 in total

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