Literature DB >> 19229912

Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition.

Robert T Yu1, Ernest E Lee, Guillaume Malik, Tomislav Rovis.   

Abstract

CO! You had me at hello: The use of chiral biphenyl-based phosphoramidite ligands on rhodium provides an efficient [2+2+2] cycloaddition between terminal alkyl alkynes and alkenyl isocyanates (see scheme). The cycloaddition proceeds through a CO migration pathway, and facilitates a rapid four-step asymmetric synthesis of indolizidine (-)-209D.

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Year:  2009        PMID： 19229912      PMCID： PMC2747357          DOI： 10.1002/anie.200805455

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  23 in total

Review 1.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2005-08-24       Impact factor: 13.423

2.  Enantioselective RH-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites.

Authors:  Lavinia Panella; Ben L Feringa; Johannes G de Vries; Adriaan J Minnaard
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

3.  Asymmetric synthesis of (-)-indolizidine 209D via B-alkyl Suzuki coupling and amination reactions.

Authors:  G Kim; S D Jung; W J Kim
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

4.  Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

5.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

Review 6.  Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

Authors:  B L Feringa
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

Review 7.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-01-03       Impact factor: 13.423

8.  Epoxide-initiated cationic cyclization of azides: a novel method for the stereoselective construction of 5-hydroxymethyl azabicyclic compounds and application in the stereo- and enantioselective total synthesis of (+)- and (-)-indolizidine 167B and 209D.

Authors:  P Ganapati Reddy; Sundarababu Baskaran
Journal:  J Org Chem       Date:  2004-04-30       Impact factor: 4.354

9.  Stereocontrolled total synthesis of potent immunosuppressant FR901483.

Authors:  Toshiyuki Kan; Teppei Fujimoto; Shigeru Ieda; Yusuke Asoh; Haruka Kitaoka; Tohru Fukuyama
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

Review 10.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-12-13       Impact factor: 13.423
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  15 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  Predictable and regioselective insertion of internal unsymmetrical alkynes in rhodium-catalyzed cycloadditions with alkenyl isocyanates.

Authors:  Rebecca Keller Friedman; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

3.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

4.  Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

Authors:  Rebecca Keller Friedman; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  Pure Appl Chem       Date:  2009-07-01       Impact factor: 2.453

5.  Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

Authors:  Wen-Zhen Zhang; John C K Chu; Kevin M Oberg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

6.  Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.

Authors:  Robert T Yu; Rebecca Keller Friedman; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

7.  Perfluorinated Taddol Phosphoramidite as an L,Z-Ligand on Rh(I) and Co(-I): Evidence for Bidentate Coordination via Metal-C6F5 Interaction.

Authors:  Derek M Dalton; Anthony K Rappé; Tomislav Rovis
Journal:  Chem Sci       Date:  2013-05-01       Impact factor: 9.825

8.  Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets.

Authors:  Stéphane Perreault; Tomislav Rovis
Journal:  Chem Soc Rev       Date:  2009-09-15       Impact factor: 54.564

9.  Enantioselective rhodium-catalyzed [2 + 2 + 2] cycloadditions of terminal alkynes and alkenyl isocyanates: mechanistic insights lead to a unified model that rationalizes product selectivity.

Authors:  Derek M Dalton; Kevin M Oberg; Robert T Yu; Ernest E Lee; Stéphane Perreault; Mark Emil Oinen; Melissa L Pease; Guillaume Malik; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

10.  Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005
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