Substituted 3-hydroxy-.delta.-lactones from epoxides

Coates, Geoffrey W.; Kramer, John W.

Title: Substituted 3-hydroxy-.delta.-lactones from epoxides

Patent · Wed Jun 14 00:00:00 EDT 2017

OSTI ID:1363768

Coates, Geoffrey W.; Kramer, John W.

Catalysts and methods for the carbonylation of epoxides to substituted 3-hydroxy-.delta.-lactones and .beta.-lactones are disclosed.

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Research Organization:: Cornell Univ., Ithaca, NY (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-05ER15687

Assignee:: Cornell University

Patent Number(s):: 9,676,743

Application Number:: 14/017,803

OSTI ID:: 1363768

Resource Relation:: Patent File Date: 2013 Sep 04

Country of Publication:: United States

Language:: English

References (30)

Substituted 3-hydroxy-delta-lactones from epoxides Coates, Geoffrey W.; Kramer, John W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8530677 US Patent Document 8,530,677	patent	September 2013
Substituted 3-hydroxy-delta-lactones from epoxides Coates, Geoffrey; Kramer, John https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100145046 US Patent Application 12/592280; 20100145046	patent-application	June 2010
Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B Aggarwal, Varinder K.; Bae, Imhyuck; Lee, Hee-Yoon Tetrahedron, Vol. 60, Issue 43 https://doi.org/10.1016/j.tet.2004.07.044	journal	October 2004
Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of α- and β-hydroxy acids and esters. Synthesis of δ- and γ-lactones Aprile, Carmela; Gruttadauria, Michelangelo; Amato, Maria E. Tetrahedron, Vol. 59, Issue 13 https://doi.org/10.1016/S0040-4020(03)00206-0	journal	March 2003
Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid Mandal, Pijus Kumar; Maiti, Gourhari; Roy, Subhas Chandra The Journal of Organic Chemistry, Vol. 63, Issue 9, p. 2829-2834 https://doi.org/10.1021/jo971526d	journal	May 1998
Transposition des oxirannes-ethanols par l'intermediaire d'alcoxyetains Bats, J. -P.; Moulines, J.; Picard, P. Tetrahedron, Vol. 38, Issue 14 https://doi.org/10.1016/0040-4020(82)85161-2	journal	January 1982
Catalytic Synthesis of β³-Amino Acid Derivatives from α-Amino Acids Byrne, Christopher M.; Church, Tamara L.; Kramer, John W. Angewandte Chemie International Edition, Vol. 47, Issue 21, p. 3979-3983 https://doi.org/10.1002/anie.200705310	journal	May 2008
Enantioselective Synthesis of Unsaturated Cyclic Tertiary Ethers By Mo-Catalyzed Olefin Metathesis Cefalo, Dustin R.; Kiely, Andrew F.; Wuchrer, Margarita Journal of the American Chemical Society, Vol. 123, Issue 13, p. 3139-3140 https://doi.org/10.1021/ja0039177	journal	April 2001
Statin Therapy-Evidence Beyond Lipid Lowering Contributing to Plaque Stability de Lorenzo, Ferruccio; Feher, Michael; Martin, Juliette Current Medicinal Chemistry, Vol. 13, Issue 28 https://doi.org/10.2174/092986706779010324	journal	December 2006
Catalytic Carbonylation of β-Lactones to Succinic Anhydrides Getzler, Yutan D. Y. L.; Kundnani, Vinod; Lobkovsky, Emil B. Journal of the American Chemical Society, Vol. 126, Issue 22, p. 6842-6843 https://doi.org/10.1021/ja048946m	journal	June 2004
Synthesis of β-Lactones: A Highly Active and Selective Catalyst for Epoxide Carbonylation Getzler, Yutan D. Y. L.; Mahadevan, Viswanath; Lobkovsky, Emil B. Journal of the American Chemical Society, Vol. 124, Issue 7, p. 1174-1175 https://doi.org/10.1021/ja017434u	journal	February 2002
First total synthesis of verbalactone, a macrocyclic dilactone isolated from Verbascum undulatum Gogoi, Siddhartha; Barua, Nabin C.; Kalita, Biswajit Tetrahedron Letters, Vol. 45, Issue 29 https://doi.org/10.1016/j.tetlet.2004.05.149	journal	July 2004
Asymmetric Catalysis Special Feature Part II: Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates Greenberg, W. A.; Varvak, A.; Hanson, S. R. Proceedings of the National Academy of Sciences, Vol. 101, Issue 16, p. 5788-5793 https://doi.org/10.1073/pnas.0307563101	journal	April 2004
Analysis of the Class I Aldolase Binding Site Architecture Based on the Crystal Structure of 2-Deoxyribose-5-phosphate Aldolase at 0.99Å Resolution Heine, Andreas; Luz, John G.; Wong, Chi-Huey Journal of Molecular Biology, Vol. 343, Issue 4 https://doi.org/10.1016/j.jmb.2004.08.066	journal	October 2004
Synthesis of the Racemate and Both Enantiomers of Massoilactone Ishikawa, Masashi; Amaike, Masayasu; Itoh, Masamichi Bioscience, Biotechnology, and Biochemistry, Vol. 67, Issue 10 https://doi.org/10.1271/bbb.67.2210	journal	January 2003
Carbonylation of Epoxides to Substituted 3-Hydroxy-δ-Lactones Kramer, John W.; Joh, Daniel Y.; Coates, Geoffrey W. Organic Letters, Vol. 9, Issue 26, p. 5581-5583 https://doi.org/10.1021/ol702475e	journal	December 2007
Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of β-hydroxycarbonyl compounds Le Sann, Christine; Muñoz, Dulce M.; Saunders, Natalie Organic & Biomolecular Chemistry, Vol. 3, Issue 9, 1719-1728 https://doi.org/10.1039/B419492F	journal	January 2005
Regioselective Hydroformylation of Allylic Alcohols Lightburn, Thomas E.; De Paolis, Omar A.; Cheng, Ka H. Organic Letters, Vol. 13, Issue 10, p. 2686-2689 https://doi.org/10.1021/ol200782d	journal	May 2011
The enantioselective synthesis of simplified southern-half fragments of soraphen A Loubinoux, Bernard; Sinnes, Jean-Luc; O'Sullivan, Anthony C. Tetrahedron, Vol. 51, Issue 12 https://doi.org/10.1016/0040-4020(95)00098-S	journal	March 1995
Enzyme-catalysed kinetic resolution of 4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one and employment of the pure enantiomers for the synthesis of anti-viral and hypocholestemic agents MacKeith, Rosemary A.; McCague, Ray; Olivo, Horacio F. Bioorganic & Medicinal Chemistry, Vol. 2, Issue 6 https://doi.org/10.1016/0968-0896(94)80005-7	journal	June 1994
Dimethyldioxirane reactions: Rate acceleration due to intramolecular H-bonding Murray, Robert W.; Gu, Hong Journal of Physical Organic Chemistry, Vol. 9, Issue 11, p. 751-758 https://doi.org/10.1002/(SICI)1099-1395(199611)9:11<751::AID-POC844>3.0.CO;2-A	journal	November 1996
Diastereoselective epoxidation of allylic alcohols by t-butyl hydroperoxide/zeolites system Palombi, Laura; Bonadies, Francesco; Scettri, Arrigo Tetrahedron, Vol. 53, Issue 33 https://doi.org/10.1016/S0040-4020(97)00718-7	journal	August 1997
Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs Ram Reddy, M. Venkat; Brown, Herbert C.; Ramachandran, P. Veeraraghavan Journal of Organometallic Chemistry, Vol. 624, Issue 1-2 https://doi.org/10.1016/S0022-328X(01)00665-9	journal	April 2001
Catalytic Double Carbonylation of Epoxides to Succinic Anhydrides: Catalyst Discovery, Reaction Scope, and Mechanism Rowley, John M.; Lobkovsky, Emil B.; Coates, Geoffrey W. Journal of the American Chemical Society, Vol. 129, Issue 16, p. 4948-4960 https://doi.org/10.1021/ja066901a	journal	April 2007
A Readily Synthesized and Highly Active Epoxide Carbonylation Catalyst Based on a Chromium Porphyrin Framework: Expanding the Range of Available β-Lactones Schmidt, Joseph A. R.; Mahadevan, Viswanath; Getzler, Yutan D. Y. L. Organic Letters, Vol. 6, Issue 3, p. 373-376 https://doi.org/10.1021/ol036244g	journal	February 2004
Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)Co ^III Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols Schaus, Scott E.; Brandes, Bridget D.; Larrow, Jay F. Journal of the American Chemical Society, Vol. 124, Issue 7, p. 1307-1315 https://doi.org/10.1021/ja016737l	journal	February 2002
Enzymatic Lactonization Stategy for Enantioselective Synthesis of a Tetrahydrolipstatin Synthon Sharma, A.; Chattopadhyay, S. J. Org. Chem., Vol. 64, Issue 22, p. 8059-8062 https://doi.org/10.1021/jo990370+		October 1999
Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors Tobert, Jonathan A. Nature Reviews Drug Discovery, Vol. 2, Issue 7, p. 517-526 https://doi.org/10.1038/nrd1112	journal	July 2003
Parallel Synthesis of a Vitamin D ₃ Library in the Solid-Phase Hijikuro, Ichiro; Doi, Takayuki; Takahashi, Takashi Journal of the American Chemical Society, Vol. 123, Issue 16, p. 3716-3722 https://doi.org/10.1021/ja003976k	journal	April 2001
Synthesis of syn - and anti -3,5-Dihydroxy-6-heptenoates from 2-Deoxy- d -ribose: Intermediates for Polyols Synthesis Zakrzewski, Peter; Lau, Cheuk K. Synlett, Issue 2, p. 0215-0218 https://doi.org/10.1055/s-2003-36801	journal	January 2003

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