Literature DB >> 21271726

Synthesis of (±)-7-hydroxylycopodine.

Hong-Yu Lin1, Barry B Snider.   

Abstract

A six step synthesis of (±)-7-hydroxylycopodine has been achieved in 5% overall yield. In the key step, a Prins cyclization of a bicyclic keto alkyne in 60% H(2)SO(4) forms a tricyclic dihydroxy amino ketone.

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Year:  2011        PMID： 21271726      PMCID： PMC3056437          DOI： 10.1021/ol200119h

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


  22 in total

Review 1.  The Lycopodium alkaloids.

Authors:  Jun'ichi Kobayashi; Hiroshi Morita
Journal:  Alkaloids Chem Biol       Date:  2005

2.  Enantioselective total synthesis of lycopodine.

Authors:  Hua Yang; Rich G Carter; Lev N Zakharov
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

3.  Total synthesis of (+)-clavolonine, (-)-deacetylfawcettiine, and (+)-acetylfawcettiine.

Authors:  Kai M Laemmerhold; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-22       Impact factor: 15.336

4.  The stereospecific total synthesis of dl-lycopodine.

Authors:  G Stork; R A Kretchmer; R H Schlessinger
Journal:  J Am Chem Soc       Date:  1968-03-13       Impact factor: 15.419

5.  The synthesis of dl-lycopodine.

Authors:  W A Ayer; W R Bowman; T C Joseph; P Smith
Journal:  J Am Chem Soc       Date:  1968-03-13       Impact factor: 15.419

6.  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

7.  Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

Authors:  Albert Padwa; Michael A. Brodney; Joseph P. Marino; Scott M. Sheehan
Journal:  J Org Chem       Date:  1997-01-10       Impact factor: 4.354

8.  Gold-catalyzed intramolecular carbocyclization of alkynyl ketones leading to highly substituted cyclic enones.

Authors:  Tienan Jin; Yoshinori Yamamoto
Journal:  Org Lett       Date:  2007-11-08       Impact factor: 6.005

9.  Syntheses in the series of Lycopodium alkaloids. IX. Two simple stereospecific syntheses of 12-epi-lycopodine.

Authors:  K Wiesner; V Musil; K J Wiesner
Journal:  Tetrahedron Lett       Date:  1968-11       Impact factor: 2.415

Review 10.  Role of huperzine a in the treatment of Alzheimer's disease.

Authors:  Alicia R Desilets; Jennifer J Gickas; Kaelen C Dunican
Journal:  Ann Pharmacother       Date:  2009-02-24       Impact factor: 3.154
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  3 in total

1.  Synthesis of (±)-7-hydroxylycopodine.

Authors:  Hong-Yu Lin; Robert Causey; Gregory E Garcia; Barry B Snider
Journal:  J Org Chem       Date:  2012-03-30       Impact factor: 4.354

2.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

3.  Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.

Authors:  Mrinmoy Saha; Rich G Carter
Journal:  Org Lett       Date:  2013-02-05       Impact factor: 6.005
  3 in total

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