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Diastereoselective Synthesis Of Highly Substituted Polycyclic Scaffolds Via A One-pot Four-step Tandem Catalytic Process

Mark W. Grafton, Stuart A. Johnson, L. Farrugia, A. Sutherland
Published 2014 · Chemistry

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A rapid and diastereoselective synthesis of highly substituted aminobicyclo[4.3.0]nonanes and bicyclo[4.4.0]decanes from alkyne derived allylic alcohols has been developed using a one-pot multi-bond forming tandem catalytic process. Overman rearrangement of the allylic trichloroacetimidates was followed by a ring closing enyne metathesis/cross metathesis sequence of reactions, in which both steps were catalysed by Grubbs second generation catalyst. The resulting exo-diene was then subjected to a hydrogen bonding directed Diels–Alder reaction forming an endo-adduct as a single diastereomer. Variation of the cross metathesis partner and dienophile allowed examination of the scope of this one-pot process and the preparation of a diverse series of highly substituted polycyclic scaffolds.
This paper references
10.1021/jo401182r
Synthesis of amino-substituted indanes and tetralins via consecutive multibond-forming tandem processes.
Mark W. Grafton (2013)
10.1021/JO052035T
Radical [n + 1] annulations with sulfur dioxide.
Anna Tsimelzon (2005)
10.1002/0471264180.OR066.01
The Allylic Trihaloacetimidate Rearrangement
L. E. Overman (2005)
10.1055/S-2008-1032111
A Rh(I)-Catalyzed Cycloisomerization Reaction Affording Cyclic Trienones
K. Brummond (2008)
10.1021/JM00144A015
Analgesic narcotic antagonists. 8. 7 alpha-Alkyl-4,5 alpha-epoxymorphinan-6-ones.
M. Kotick (1981)
10.1039/c2cc33649a
Discovery of a multi-bond forming, four-step tandem process: construction of drug-like polycyclic scaffolds.
Mark W. Grafton (2012)
10.1021/JO026828G
Intramolecular Pauson−Khand Reactions of α,β-Unsaturated Esters and Related Electron-Deficient Olefins
M. Rivero (2003)
10.1055/S-1998-1808
POLYMER BOUND 3,5-CYCLOHEXADIENE-1,2-DIOLS AS CORE STRUCTURES FOR THE DEVELOPMENT OF SMALL MOLECULE LIBRARIES
S. Wendeborn (1998)
10.1002/EJOC.201100438
Enyne‐Metathesis‐Based Tandem Processes
Jing-wei Li (2011)
10.1039/c1ob06086d
Efficient approach to novel 1α-triazolyl-5α-androstane derivatives as potent antiproliferative agents.
Zalán Kádár (2011)
10.1021/OL048621A
Nankakurine A, a novel C16N2-type alkaloid from Lycopodium hamiltonii.
Y. Hirasawa (2004)
10.1021/JO026433X
A modular synthesis of annonaceous acetogenins.
J. Marshall (2003)
10.1016/J.TET.2006.06.063
Netamines A–G: seven new tricyclic guanidine alkaloids from the marine sponge Biemna laboutei
Hagit Sorek (2006)
10.1016/S0040-4039(00)96405-0
Stereoselective synthetic approaches to arylpolyene isobutylamides
R. J. Blade (1987)
10.1002/(SICI)1521-3773(19981002)37:18<2459::AID-ANIE2459>3.0.CO;2-O
Stereoselective Allylic C-H Activation with Tertiary Alkylboranes: A New Method for Preparing Cycloalkyl Derivatives with Three Adjacent Stereocenters.
F. Lhermitte (1998)
10.1021/ol201336x
Total synthesis of isofregenedadiol.
Suresh E. Kurhade (2011)
10.1021/jo101619d
Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
R. A. Altman (2010)
10.1021/JO000997O
Synthesis of isoindolo[2,1-alpha]indoles by the palladium-catalyzed annulation of internal acetylenes.
K. R. Roesch (2001)
10.1021/jo201794k
Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: total synthesis of (+)-sertraline.
S. Lee (2011)
10.1016/S0040-4020(01)96701-8
A stereorational total synthesis of (−)-ptilocaulin
A. E. Walts (1985)
10.1021/JO981715B
INTRAMOLECULAR CYCLIZATIONS OF ENYNES USING RUCLH(CO)(PPH3)3
M. Nishida (1998)
10.1039/B503816B
Rh(I)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides
K. Fuji (2005)
10.1002/EJOC.201000001
Synthesis of a Novel Taxa‐Oxa‐Sugar Hybrid Core Structure by Tandem Cross‐Enyne Metathesis/IMDA
Rahul S. Nandurdikar (2010)
10.1002/chem.201200835
1,7-octadiene-assisted tandem multicomponent cross-enyne metathesis (CEYM)-Diels-Alder reactions: a useful alternative to Mori's conditions.
S. Fustero (2012)
10.1021/JO00260A014
Acid-catalyzed reactions of hapalindoles
R. Bonjouklian (1988)
10.1021/OL035194C
One-pot three-component tandem metathesis/Diels-Alder reaction.
H. Lee (2003)
10.1021/JA00034A036
Total synthesis of the latrunculins
A. Smith (1992)
10.1016/j.bmc.2012.01.008
A facile 'click' approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro.
Zalán Kádár (2012)



This paper is referenced by
10.1039/c6ob00165c
A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(II)- and ruthenium(II)-catalysis.
Mohamed A. B. Mostafa (2016)
10.1021/acs.joc.5b00583
One-Pot Synthesis of 5-Amino-2,5-dihydro-1-benzoxepines: Access to Pharmacologically Active Heterocyclic Scaffolds.
Ewen D. D. Calder (2015)
10.1002/CHIN.201509054
Diastereoselective Synthesis of Highly Substituted Polycyclic Scaffolds via a One-Pot Four-Step Tandem Catalytic Process.
Mark W. Grafton (2015)
10.1002/EJOC.201403482
Synthesis of Acyloxy‐Semicyclic Dienes Using an Enyne Metathesis/Ring Closing Metathesis Approach
J. Kueh (2015)
10.1021/acs.joc.6b01357
Synthesis of 5-Amino-2,5-dihydro-1H-benzo[b]azepines Using a One-Pot Multibond Forming Process.
S. A. I. Sharif (2016)
10.1002/cctc.201800525
Assisted Tandem Catalytic Conversion of Acrylates into Adipic Esters
P. Maity (2018)
10.1021/ACS.JOC.6B01881
Synthesis of Allylic Amide Functionalized 2H-Chromenes and Coumarins Using a One-Pot Overman Rearrangement and Gold(I)-Catalyzed Hydroarylation.
S. A. I. Sharif (2016)
10.1016/J.CCR.2015.09.012
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014
J. W. Herndon (2016)
10.1039/c7ob00456g
Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates.
Mohamed A. B. Mostafa (2017)
10.1039/c6ob02625g
Recent advances in the Overman rearrangement: synthesis of natural products and valuable compounds.
R. A. Fernandes (2017)
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