Literature DB >> 23384410

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

Mrinmoy Saha1, Rich G Carter.   

Abstract

The enantioselective syntheses of 10-hydroxylycopodine, deacetylpaniculine, and paniculine have been accomplished through use of a common intermediate. Key steps in the synthetic sequence toward these lycopodium alkaloids include formation of the tricyclic core via a conformationally accelerated, intramolecular Mannich cyclization and an organocatalyzed, intramolecular Michael addition to form the C(7)-C(12) linkage.

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Year:  2013        PMID： 23384410      PMCID： PMC3616490          DOI： 10.1021/ol303272w

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


  22 in total

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

Authors:  Hong-Yu Lin; Barry B Snider
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis.

Authors:  M Tokunaga; J F Larrow; F Kakiuchi; E N Jacobsen
Journal:  Science       Date:  1997-08-15       Impact factor: 47.728

3.  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

4.  Asymmetric total synthesis of clavolonine.

Authors:  Kenji Nakahara; Kie Hirano; Ryota Maehata; Yasuyuki Kita; Hiromichi Fujioka
Journal:  Org Lett       Date:  2011-03-09       Impact factor: 6.005

5.  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

6.  Expedient enantioselective synthesis of cermizine D.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Rich G Carter
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

7.  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

8.  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

9.  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

10.  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
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  2 in total

1.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

2.  Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Authors:  Yi-Yun Yu; Gunda I Georg
Journal:  Adv Synth Catal       Date:  2014-04-14       Impact factor: 5.837
  2 in total

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