Literature DB >> 22201223

Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.

Rebecca A Murphy1, Richmond Sarpong.   

Abstract

A concise enantioselective approach to the tetracyclic core of the magellanine-type Lycopodium alkaloids is reported. Key to this approach is the use of the Hajos-Parrish reaction to set a challenging quaternary stereocenter, thereby guiding the stereoselectivity for the remainder of the synthesis, as well as the use of a palladium-mediated direct pyridine functionalization reaction to forge the tetracyclic core.
© 2011 American Chemical Society

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Year:  2011        PMID： 22201223      PMCID： PMC3262889          DOI： 10.1021/ol203269f

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


  10 in total

1.  Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation.

Authors:  Domingo García-Cuadrado; Ataualpa A C Braga; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

2.  Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.

Authors:  Kimberly K Larson; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

3.  Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.

Authors:  Vishnumaya Bisai; Richmond Sarpong
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

Review 4.  The Lycopodium alkaloids.

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

5.  Palladium-catalyzed direct arylation of azine and azole N-oxides: reaction development, scope and applications in synthesis.

Authors:  Louis-Charles Campeau; David R Stuart; Jean-Philippe Leclerc; Mégan Bertrand-Laperle; Elisia Villemure; Ho-Yan Sun; Sandrine Lasserre; Nicolas Guimond; Melanie Lecavallier; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

6.  Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.

Authors:  Alakesh Bisai; Scott P West; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

7.  Biaryl synthesis via direct arylation: establishment of an efficient catalyst for intramolecular processes.

Authors:  Louis-Charles Campeau; Mathieu Parisien; Melissa Leblanc; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2004-08-04       Impact factor: 15.419

8.  Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation: substituent effects.

Authors:  Domingo García-Cuadrado; Paula de Mendoza; Ataualpa A C Braga; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2007-04-27       Impact factor: 15.419

9.  Synthesis of 7a-substituted Hajos-Wiechert ketone analogues.

Authors:  Jason W J Kennedy; Sophia Vietrich; Hilmar Weinmann; Dominic E A Brittain
Journal:  J Org Chem       Date:  2008-06-10       Impact factor: 4.354

10.  Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions.

Authors:  Takashi Kozaka; Naoki Miyakoshi; Chisato Mukai
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354
  10 in total
  2 in total

1.  Synthetic studies toward the citrinadin A and B core architecture.

Authors:  Devon A Mundal; Richmond Sarpong
Journal:  Org Lett       Date:  2013-09-19       Impact factor: 6.005

2.  Synthetic studies on pseudo-dimeric Lycopodium alkaloids: total synthesis of complanadine B.

Authors:  James N Newton; Daniel F Fischer; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-10       Impact factor: 15.336
  2 in total

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