Literature DB >> 16238304

A model study toward the total synthesis of N-deacetyllappaconitine.

Douglass F Taber1, Jiang-Lin Liang, Bei Chen, Lisi Cai.   

Abstract

[reaction: see text] A model study leading to the preparation of the AEF rings of N-deacetyllappaconitine is described. The conjugate addition to the alpha-alkyl cyclohexenone 10 proceeded with high diastereocontrol. The Mannich cyclization of 16 to 4 was accomplished by heating with Rexyn-300 and Na(2)SO(4).

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Year:  2005        PMID: 16238304      PMCID: PMC3248817          DOI: 10.1021/jo051155y

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  13 in total

Review 1.  Diterpenoid and steroidal alkaloids.

Authors:  M I Choudhary
Journal:  Nat Prod Rep       Date:  1999-10       Impact factor: 13.423

2.  A convenient chiron for substituted cyclohexanones.

Authors:  D F Taber; T E Christos; M Rahimizadeh; B Chen
Journal:  J Org Chem       Date:  2001-08-24       Impact factor: 4.354

3.  A Tandem Horner-Emmons Olefination-Conjugate Addition Approach to the Synthesis of 1,5-Disubstituted-6-azabicyclo[3.2.1]octanes Based on the AE Ring Structure of the Norditerpenoid Alkaloid Methyllycaconitine.

Authors:  David J. Callis; Noel F. Thomas; David P. J. Pearson; Barry V. L. Potter
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

4.  Synthesis of the eight enantiomerically pure diastereomers of the 12-F(2)-isoprostanes.

Authors:  Douglass F Taber; Ming Xu; John C Hartnett
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

5.  The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-01       Impact factor: 15.336

6.  Total synthesis of (+/-)-aspidospermidine.

Authors:  M A Toczko; C H Heathcock
Journal:  J Org Chem       Date:  2000-05-05       Impact factor: 4.354

Review 7.  Diterpenoid and steroidal alkaloids.

Authors:  M I Choudhary
Journal:  Nat Prod Rep       Date:  1995-08       Impact factor: 13.423

8.  Synthesis of (-)-tetrodotoxin: preparation of an advanced cyclohexenone intermediate.

Authors:  Douglass F Taber; Pierre H Storck
Journal:  J Org Chem       Date:  2003-10-03       Impact factor: 4.354

9.  Bridgehead arylation: a direct route to advanced intermediates for the synthesis of C-20 diterpene alkaloids.

Authors:  Craig M Williams; Lewis N Mander
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

10.  Effect of diterpenoid alkaloids on cardiac sympathetic efferent and vagal afferent nerve activity.

Authors:  H Chiao; S W Pelletier; H K Desai; W R Rebagay; R W Caldwell
Journal:  Eur J Pharmacol       Date:  1995-09-05       Impact factor: 4.432

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  3 in total

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Journal:  ACS Cent Sci       Date:  2021-07-27       Impact factor: 14.553

2.  Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine.

Authors:  Yuan Shi; Jeremy T Wilmot; Lars Ulrik Nordstrøm; Derek S Tan; David Y Gin
Journal:  J Am Chem Soc       Date:  2013-09-16       Impact factor: 15.419

3.  Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process.

Authors:  Koichi Hagiwara; Toshiki Tabuchi; Daisuke Urabe; Masayuki Inoue
Journal:  Chem Sci       Date:  2016-03-18       Impact factor: 9.825

  3 in total

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