Literature DB >> 26257443

Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes.

Sarah M Wells1, Kay M Brummond1.   

Abstract

The direct installation of the C4 and C10 methyl groups present in the 6,12-guaianolide framework using a Rh(I)-catalyzed cyclocarbonylation reaction of methyl subsituted allenes and alkynes is described. High yields of bicyclo[5.3.0]decanes are afforded when low reaction concentrations involving syringe pump addition of the allene-yne to the catalyst are used.

Entities:  

Keywords:  Allene-yne; Bicyclo[5.3.0]decadienone; Guaianolide; High Dilution; Pauson-Khand; Solid-supported Scavenger

Year:  2015        PMID： 26257443      PMCID： PMC4525719          DOI： 10.1016/j.tetlet.2015.01.075

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  An allenic Pauson-Khand approach to 6,12-guaianolides.

Authors:  Francois Grillet; Chaofeng Huang; Kay M Brummond
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.

Authors:  Merle A Battiste; Phillip M Pelphrey; Dennis L Wright
Journal:  Chemistry       Date:  2006-04-24       Impact factor: 5.236

Review 3.  Perspectives on sesquiterpene lactones in inflammation and cancer.

Authors:  Irmgard Merfort
Journal:  Curr Drug Targets       Date:  2011-10       Impact factor: 3.465

4.  Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes.

Authors:  Hermann A Wegner; Armin de Meijere; Paul A Wender
Journal:  J Am Chem Soc       Date:  2005-05-11       Impact factor: 15.419

5.  Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB.

Authors:  Bettina Siedle; Alfonso J García-Piñeres; Renato Murillo; Jürgen Schulte-Mönting; Victor Castro; Peter Rüngeler; Christoph A Klaas; Fernando B Da Costa; Wanda Kisiel; Irmgard Merfort
Journal:  J Med Chem       Date:  2004-11-18       Impact factor: 7.446

6.  An allenic Pauson-Khand-type reaction: a reversal in pi-bond selectivity and the formation of seven-membered rings.

Authors:  Kay M Brummond; Hongfeng Chen; Kimberly D Fisher; Angela D Kerekes; Brenden Rickards; Peter C Sill; Steven J Geib
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

7.  Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

Authors:  Scott E Denmark; Joseck M Muhuhi
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

8.  Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors:  Francois Grillet; Kay M Brummond
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354

9.  Total synthesis of (+)-achalensolide based on the rh(i)-catalyzed allenic Pauson-Khand-type reaction.

Authors:  Toshiyuki Hirose; Naoki Miyakoshi; Chisato Mukai
Journal:  J Org Chem       Date:  2007-12-28       Impact factor: 4.354

10.  A redox economical synthesis of bioactive 6,12-guaianolides.

Authors:  Bo Wen; Joseph K Hexum; John C Widen; Daniel A Harki; Kay M Brummond
Journal:  Org Lett       Date:  2013-05-10       Impact factor: 6.005
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  2 in total

1.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

2.  Synthesis of Guaianolide Analogues with a Tunable α-Methylene-γ-lactam Electrophile and Correlating Bioactivity with Thiol Reactivity.

Authors:  Paul A Jackson; Henry A M Schares; Katherine F M Jones; John C Widen; Daniel P Dempe; Francois Grillet; Matthew E Cuellar; Michael A Walters; Daniel A Harki; Kay M Brummond
Journal:  J Med Chem       Date:  2020-11-17       Impact factor: 7.446
  2 in total

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