Diastereoselective synthesis of (±) -heliotropamide by a one-pot, four-component reaction
Younai, A.; Chin, G.F.; Shaw, J.T.
Journal of Organic Chemistry 75(23): 8333-8336
2010
ISSN/ISBN: 1520-6904
PMID: 21062051
DOI: 10.1021/jo1019317
Accession: 052591851
The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.
PDF emailed within 0-6 h: $19.90
Related References
Wei, J.; Shaw, J.T. 2007: Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction Organic Letters 9(20): 4077-4080Cao, J.; Sun, J.; Yan, C.-G. 2018: Regioselective and diastereoselective synthesis of two functionalized 1,5-methanoindeno[1,2-d]azocines via a three-component reaction Organic and Biomolecular Chemistry 16(22): 4170-4175
Galliford, C.V.; Martenson, J.S.; Stern, C.; Scheidt, K.A. 2007: A highly diastereoselective, catalytic three-component assembly reaction for the synthesis of spiropyrrolidinyloxindoles Chemical Communications 6: 631-633
Yadav, J.S.; Reddy, B.V.Subba; Aravind, S.; Kumar, G.G.K.S.Narayana; Madhavi, C.; Kunwar, A.C. 2008: Three-component, one-pot diastereoselective synthesis of 4-amidotetrahydropyrans via the Prins-Ritter reaction sequence Tetrahedron 64(13): 3025-3031
Ahadi, S.; Zolghadr, M.; Khavasi, H.R.; Bazgir, A. 2013: A diastereoselective synthesis of pyrano fused coumarins via organocatalytic three-component reaction Organic and Biomolecular Chemistry 11(2): 279-286
Nair, V.; Sreekanth, A.R.; Abhilash, N.; Bhadbhade, M.M.; Gonnade, R.C. 2002: A novel three-component reaction for the diastereoselective synthesis of 2H-pyrimido[2,1-a]isoquinolines via 1,4-dipolar cycloaddition Organic Letters 4(21): 3575-3577
Carson, C.A.; Kerr, M.A. 2005: Diastereoselective synthesis of pyrrolidines via the Yb(OTf)3 catalyzed three-component reaction of aldehydes, amines, and 1,1-cyclopropanediesters Journal of Organic Chemistry 70(20): 8242-8244
Tabibi, T.; Esmaeili, A.A.; Mague, J.T. 2022: An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction Molecular Diversity 26(1): 183-190
Zhang, X.; Qiu, W.; Murray, S.A.; Zhan, D.; Evans, J.; Jasinski, J.P.; Wang, X.; Zhang, W. 2021: Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s Journal of Organic Chemistry 86(23): 17395-17403
Ao, C.; Huang, J.; Xu, X.; Jia, S.; Kang, Z.; Hu, W. 2020: A Rh-catalyzed three-component reaction for the diastereoselective synthesis of pyrazolone derivatives with contiguous quaternary stereocenters Organic and Biomolecular Chemistry 18(18): 3466-3470
Xiong, F.; Wang, H.; Yan, L.; Xu, L.; Tao, Y.; Wu, Y.; Chen, F. 2015: Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction Organic and Biomolecular Chemistry 13(38): 9813-9819
Maiti, S.; Menéndez, J.C. 2011: Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction Chemical Communications 47(38): 10554-10556
Angyal, A.ó; Demjén, A.ás.; Wéber, E.; Kovács, A.K.; Wölfling, J.án.; Puskás, L.ás.ó G.; Kanizsai, I.án. 2018: Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2 H-Azirines via Joullié-Ugi Three-Component Reaction Journal of Organic Chemistry 83(7): 3570-3581
Gurumurthy, C.; Fatima, N.; Reddy, G.N.; Kumar, C.G.; Sabitha, G.; Ramakrishna, K.V.S. 2016: A diastereoselective synthesis of tetrahydro- and dihydro-pyrido[2,3-c]coumarin derivatives via a one-pot three-component Povarov reaction catalyzed by bismuth(III) chloride Bioorganic and Medicinal Chemistry Letters 26(20): 5119-5125
Alcaide, B.; Almendros, P.; Aragoncilio, C.; Callejo, R.; Ruiz, M.P.; Rosario Torres, M. 2012: Diastereoselective Synthesis of β-Lactam-Oxindole Hybrids Through a Three-Component Reaction of Azetidine-2,3-diones, α-Diazo-oxindoles, and Alcohols Catalyzed by [Rh2(OAC)4] European Journal of Organic Chemistry (12): 2359-2366
Rondot, C.; Zhu, J. 2005: Synthesis of chiral vicinal diamines by highly diastereoselective three-component phenolic Mannich reaction: temperature-dependent stereodivergency Organic Letters 7(8): 1641-1644
Wang, Y.; Zhu, Y.; Chen, Z.; Mi, A.; Hu, W.; Doyle, M.P. 2003: A novel three-component reaction catalyzed by dirhodium(II) acetate: decomposition of phenyldiazoacetate with arylamine and imine for highly diastereoselective synthesis of 1,2-diamines Organic Letters 5(21): 3923-3926
Ribelles, P.; Sridharan, V.; Villacampa, M.; Ramos, M.T.; Menéndez, J.C. 2013: Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA'BC sequential four-component reaction and their application to 2-arylquinoline synthesis Organic and Biomolecular Chemistry 11(4): 569-579
Deshmukh, S.C.; Roy, A.; Talukdar, P. 2012: Diastereoselective construction of syn-α-oxyamines via three-component α-oxyaldehyde-dibenzylamine-alkyne coupling reaction: application in the synthesis of (+)-β-conhydrine and its analogues Organic and Biomolecular Chemistry 10(37): 7536-7544
Teimouri, M.B.; Mokhtare, Z.; Khavasi, H.R. 2021: Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels-Alder cycloaddition and Michael addition Organic and Biomolecular Chemistry 19(11): 2517-2525