Literature DB >> 19102683

Reaction discovery employing macrocycles: transannular cyclizations of macrocyclic bis-lactams.

Chong Han1, Sathish Rangarajan, Alicia C Voukides, Aaron B Beeler, Richard Johnson, John A Porco.   

Abstract

Macrocyclic bis-lactams have been synthesized by cyclodimerization of homoallylic amino esters employing a Zr(IV)-catalyzed ester-amide exchange protocol. Base-mediated transannular cyclizations have been identified to access both bicyclic [5-11] and tricyclic [5-8-5] frameworks in good yield and diastereoselectivity. Preliminary mechanistic studies support an olefin isomerization-intramolecular conjugate addition pathway.

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Year:  2009        PMID： 19102683      PMCID： PMC2774802          DOI： 10.1021/ol802729f

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


  22 in total

1.  Unnatural natural products from the transannular cyclization of lathyrane diterpenes.

Authors:  G Appendino; G C Tron; T Jarevång; O Sterner
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

2.  Macrolactones in diversity-oriented synthesis: preparation of a pilot library and exploration of factors controlling macrocyclization.

Authors:  Darby R Schmidt; Ohyun Kwon; Stuart L Schreiber
Journal:  J Comb Chem       Date:  2004 Mar-Apr

3.  Synthesis of a library of complex macrodiolides employing cyclodimerization of hydroxy esters.

Authors:  Aaron B Beeler; Dayle E Acquilano; Qibin Su; Feng Yan; Bryan L Roth; James S Panek; John A Porco
Journal:  J Comb Chem       Date:  2005 Sep-Oct

Review 4.  Advancing chemistry and biology through diversity-oriented synthesis of natural product-like libraries.

Authors:  Shiying Shang; Derek S Tan
Journal:  Curr Opin Chem Biol       Date:  2005-06       Impact factor: 8.822

5.  Asymmetric synthesis of salvinorin A, a potent kappa opioid receptor agonist.

Authors:  Jonathan R Scheerer; Jonathan F Lawrence; Grace C Wang; David A Evans
Journal:  J Am Chem Soc       Date:  2007-06-30       Impact factor: 15.419

6.  From macrocycle dipeptide lactams to azabicyclo[X.Y.0]alkanone amino acids: a transannular cyclization route for peptide mimic synthesis.

Authors:  Simon Surprenant; William D Lubell
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

7.  Gold(I)-catalyzed intramolecular hydroamination of unactivated alkenes with carboxamides.

Authors:  Christopher F Bender; Ross A Widenhoefer
Journal:  Chem Commun (Camb)       Date:  2006-08-23       Impact factor: 6.222

8.  Thermal [1,5] hydrogen sigmatropic shifts in cis,cis-1,3-cyclononadienes probed by gas-phase kinetic studies and density functional theory calculations.

Authors:  John E Baldwin; Anuradha S Raghavan; B Andes Hess; Lidia Smentek
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

9.  Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Authors:  Mary M Rozenman; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-11-10       Impact factor: 15.419

10.  Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolides.

Authors:  Qibin Su; Aaron B Beeler; Emil Lobkovsky; John A Porco; James S Panek
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005
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  6 in total

1.  Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Authors:  John R Goodell; Jennifer L Poole; Aaron B Beeler; Jeffrey Aubé; John A Porco
Journal:  J Org Chem       Date:  2011-11-01       Impact factor: 4.354

2.  Multidimensional Screening and Methodology Development for Condensations Involving Complex 1,2-Diketones.

Authors:  John R Goodell; Bo Leng; Tracy K Snyder; Aaron B Beeler; John A Porco
Journal:  Synthesis (Stuttg)       Date:  2010-07-01       Impact factor: 3.157

3.  Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence.

Authors:  Spandan Chennamadhavuni; James S Panek; John A Porco; Lauren E Brown
Journal:  J Org Chem       Date:  2018-12-05       Impact factor: 4.354

4.  Synthesis of a novel chemotype via sequential metal-catalyzed cycloisomerizations.

Authors:  Bo Leng; Stephanie Chichetti; Shun Su; Aaron B Beeler; John A Porco
Journal:  Beilstein J Org Chem       Date:  2012-08-20       Impact factor: 2.883

5.  Remodelling of the natural product fumagillol employing a reaction discovery approach.

Authors:  Bradley R Balthaser; Meghan C Maloney; Aaron B Beeler; John A Porco; John K Snyder
Journal:  Nat Chem       Date:  2011-12       Impact factor: 24.427

6.  Macrocycles: lessons from the distant past, recent developments, and future directions.

Authors:  Andrei K Yudin
Journal:  Chem Sci       Date:  2014-11-03       Impact factor: 9.825
  6 in total

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