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Marco Ciufolini

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Research and Teaching Interests

Research in this group is directed toward the total synthesis of nitrogenous natural products that possess interesting structures and useful biological activities. In the course of these endeavors, great emphasis is placed on the development of innovative, efficient, and environmentally responsible preparative reactions. Possibilities are currently being sought in areas as diverse as main-group, transition-, and f-block organometallic chemistry; enzymatic transformations; photochemistry; heterocycles; hypervalent iodine chemistry, etc. Problems of current interest encompass the synthesis of thiopeptide antibiotics (genetic modulators and inhibitors of protein synthesis); of polyoxazole natural products, e.g. telomestatin (potent and selective inhibitor of human telomerase); of substances incorporating medium-ring nitrogen heterocycles or surrogates thereof; e.g. mitomycinoids (antitumor agents); and of spirocyclic alkaloids (immunusuppressants; cytotoxic agents; ion-channel blockers; and so on). These substances are of great interest in oncology, neurology, microbiology, immunology, and genetics. Our research is thus especially relevant to the objectives of UBC's Drug Research Institute, an exciting multidisciplinary initiative, and of the pharmaceutical industry.

Several compounds of current interest in this group are shown below.

Ciufolini Group Research: Natural Product Synthesis

Contact

Real name: 
Marco Ciufolini
Email: 
Office Room Number(s): 
Chemistry A337
Office Phone Number: 
604-822-2419
Fax Number: 
604-822-2847

Curriculum Vitae

 B.S. (chemistry) 1978, Spring Hill College, Mobile AL; Ph.D. 1981, University of Michigan, Ann Arbor MI (M. Koreeda); Postdoc 1982-84, Yale University, New Haven, CT (S. Danishefsky). A. P. Sloan Fellow, 1994-98; Merck & Co. Academic Development Prize, 2001-2. Canada Research Chair in Synthetic Organic Chemistry, 2004

Publications

2015

Paladino, M. ; Zaifman, J. ; Ciufolini, M. A. Total Synthesis Of (+)-3-Demethoxyerythratidinone And (+)-Erysotramidine Via The Oxidative Amidation Of A Phenol. ORGANIC LETTERS 2015, 17, 3422-3425.
Tropak, M. B. ; Zhang, J. ; Yonekawa, S. ; Rigat, B. A. ; Aulakh, V. S. ; Smith, M. R. ; Hwang, H. - J. ; Ciufolini, M. A. ; Mahuran, D. J. Pyrimethamine Derivatives: Insight Into Binding Mechanism And Improved Enhancement Of Mutant Beta-N-Acetylhexosaminidase Activity. JOURNAL OF MEDICINAL CHEMISTRY 2015, 58, 4483-4493.
Xu, S. ; Ciufolini, M. A. Formal Synthesis Of (+/-)-Tetrodotoxin Via The Oxidative Amidation Of A Phenol: On The Structure Of The Sato Lactone. ORGANIC LETTERS 2015, 17, 2424-2427.
Hwang, H. - J. ; Ciufolini, M. A. A Route To The Heterocyclic Cluster Of The E-Series Of Thiopeptide Antibiotics. JOURNAL OF ORGANIC CHEMISTRY 2015, 80, 4184-4188.
Jain, N. ; Ciufolini, M. A. Oxidative Amidation In The Naphthalene Series. SYNLETT 2015, 26, 631-634.

2014

Ciufolini, M. A. Synthetic Studies On Heterocyclic Natural Products. Can. J. Chem. 2014, 91.
Kasahara, T. ; Jang, Y. J. ; Racicot, L. ; Panagopoulos, D. ; Liang, S. H. ; Ciufolini, M. A. Iodonium Metathesis Reactions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2014, 53, 9637-9639.
Racicot, L. ; Kasahara, T. ; Ciufolini, M. A. Arylation Of Diorganochalcogen Compounds With Diaryliodonium Triflates: Metal Catalysts Are Unnecessary. ORGANIC LETTERS 2014, 16, 6382-6385.

2013

Chau, J. ; Xu, S. ; Ciufolini, M. A. Assembly Of A Key Dienic Intermediate For Tetrodotoxin Via A Machetti-Desarlo Reaction. JOURNAL OF ORGANIC CHEMISTRY 2013, 78, 11901-11910.
Tam, Y. Yi C. ; Chen, S. ; Zaifman, J. ; Tam, Y. K. ; Lin, P. J. C. ; Ansell, S. ; Roberge, M. ; Ciufolini, M. A. ; Cullis, P. R. Small Molecule Ligands For Enhanced Intracellular Delivery Of Lipid Nanoparticle Formulations Of Sirna. NANOMEDICINE-NANOTECHNOLOGY BIOLOGY AND MEDICINE 2013, 9, 665-674.
Smith, M. R. ; Kim, J. Yun; Ciufolini, M. A. Pd-Arylurea Complexes For The Heck Arylation Of Crotonic And Cinnamic Substrates. TETRAHEDRON LETTERS 2013, 54, 2042-2045.
Lin, P. J. C. ; Tam, Y. Yi C. ; Hafez, I. ; Sandhu, A. ; Chen, S. ; Ciufolini, M. A. ; Nabi, I. R. ; Cullis, P. R. Influence Of Cationic Lipid Composition On Uptake And Intracellular Processing Of Lipid Nanoparticle Formulations Of Sirna. NANOMEDICINE-NANOTECHNOLOGY BIOLOGY AND MEDICINE 2013, 9, 233-246.
Kasahara, T. ; Ciufolini, M. A. Further Studies Toward Himandrine Via Sequential Oxidative Amidation - Intramolecular Diels-Alder Reactions. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE 2013, 91, 82-90.
Smith, M. R. ; Jang, Y. Jin; Kim, J. Yun; Ciufolini, M. A. Selective Reactivity Of Electron-Rich Aryl Iodides In The Heck Arylation Of Disubstituted Alkenes Catalyzed By Palladium-Arylurea Complexes. TETRAHEDRON 2013, 69, 10139-10151.
Chau, J. ; Ciufolini, M. A. Bimolecular Oxidative Amidation Of Phenols: 1-(Acetylamino)4-Oxo-2,5-Cyclohexadiene-1-Acetic Acid, Methyl Ester. Org. Syn. 2013, 90, 190.

2012

Turner, C. Dylan; Ciufolini, M. A. Useful Building Blocks For The Stereocontrolled Assembly Of 2,3,5-Trisubstituted Pyrrolidines. HETEROCYCLES 2012, 85, 85-94.
Braud, S. ; Ciufolini, M. A. ; Harosh, I. Enteropeptidase: A Gene Associated With A Starvation Human Phenotype And A Novel Target For Obesity Treatment. PLOS ONE 2012, 7, e49612.
Turner, C. Dylan; Ciufolini, M. A. ``extreme'' Ugi Reactions With Some Complex Alpha-Amino Acids. ORGANIC LETTERS 2012, 14, 4970-4973.
Lee, J. B. ; Zhang, K. ; Tam, Y. Yi C. ; Tam, Y. K. ; Belliveau, N. M. ; Sung, V. Y. C. ; Lin, P. J. C. ; LeBlanc, E. ; Ciufolini, M. A. ; Rennie, P. S. ; Cullis, P. R. Lipid Nanoparticle Sirna Systems For Silencing The Androgen Receptor In Human Prostate Cancer In Vivo. INTERNATIONAL JOURNAL OF CANCER 2012, 131, E781-E790.

2011

Kim, S. ; Ciufolini, M. A. Complete Facial Selectivity In The Diels-Alder Reaction Of A 5-Amino-5-Carboxycyclopentadiene Derivative. ORGANIC LETTERS 2011, 13, 3274-3277.
Aulakh, V. S. ; Ciufolini, M. A. Total Synthesis And Complete Structural Assignment Of Thiocillin I. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2011, 133, 5900-5904.
Turner, C. D. ; Ciufolini, M. A. Ugi Reactions At The Limit: A Modular Approach To The Tetrahydroisoquinoline Natural Products. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2011, 241}, Meeting Abstract = {79-ORGN.
Zhang, J. ; Coqueron, P. - Y. ; Ciufolini, M. A. Development And Applications Of An Oxazole-Forming Reaction. HETEROCYCLES 2011, 82, 949+.
Zhang, J. ; Ciufolini, M. A. An Approach To The Bis-Oxazole Macrocycle Of Diazonamides. ORGANIC LETTERS 2011, 13, 390-393.
Jen, T. ; Mendelsohn, B. A. ; Ciufolini, M. A. Oxidation Of Alpha-Oxo-Oximes To Nitrile Oxides With Hypervalent Iodine Reagents. JOURNAL OF ORGANIC CHEMISTRY 2011, 76, 728-731.
Liang, H. ; Ciufolini, M. A. Chiral Hypervalent Iodine Reagents In Asymmetric Reactions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2011, 50, 11849-11851.
Turner, C. Dylan; Ciufolini, M. A. Oxidation Of Oximes With Hypervalent Iodine Reagents: Opportunities, Development, And Applications. ARKIVOC 2011, 410-428.
Basha, G. ; Novobrantseva, T. ; Rosin, N. ; Ciufolini, M. ; Tam, Y. Y. C. ; Hafez, I. M. ; Wong, M. ; Sugo, T. ; Ruda, V. ; Klebanov, B. ; Qin, J. ; Akinc, A. ; J., H. ;M. ; Cullis, P. R. Influence Of Cationic Lipid Composition On Uptake, Intracellular Trafficking And Gene Silencing Properties Of Lipid Nanoparticle Formulations Of Sirna In Primary Antigen Presenting Cells. Molecular Theraphy 2011, 19, 2186.
Turner, C. Dylan; Ciufolini, M. A. Directed Aromatic Functionalization In Natural-Product Synthesis: Fredericamycin A, Nothapodytine B, And Topopyrones B And D. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 2011, 7, 1475-1485.
Chau, J. ; Ciufolini, M. A. The Chemical Synthesis Of Tetrodoxin: An Ongoing Quest. MARINE DRUGS 2011, 9, 2046-2074.

2010

Zhang, J. ; Ciufolini, M. A. A Direct Route To 2-Alkyl-4-Carbethoxy-5-Vinyloxazoles. Tetrahedron Letters 2010, 51, 4699 - 4701.
Liang, H. ; Zhou, Y. ; Ciufolini, M. A. Heck Reaction Of Amino Acid Derived Vinyl Substrates In The Synthesis Of Homotyrosinol Derivatives. Synthesis 2010, 2515 - 2520.
Braud, S. ; Ciufolini, M. ; Harosh, I. `energy Expenditure Genes' Or `energy Absorption Genes': A New Target For The Treatment Of Obesity And Type Ii Diabetes. FUTURE MEDICINAL CHEMISTRY 2010, 2, 1777-1783.
Ciufolini, M. A. ; Lefranc, D. Micrococcin P1: Structure, Biology And Synthesis. Natural Product Reports 2010, 27, 330 - 342.
Zhigaltsev, I. V. ; Winters, G. ; Srinivasulu, M. ; Crawford, J. ; Wong, M. ; Amankwa, L. ; Waterhouse, D. ; Masin, D. ; Webb, M. ; Harasym, N. ; Heller, L. ; Bally, M. B. ; Ciufolini, M. A. ; Cullis, P. R. ; Maurer, N. Development Of A Weak-Base Docetaxel Derivative That Can Be Loaded Into Lipid Nanoparticles. JOURNAL OF CONTROLLED RELEASE 2010, 144, 332-340.
Liang, H. ; Ciufolini, M. A. Oxidative Spirocyclization Of Phenolic Sulfonamides: Scope And Applications. Chemistry (Weinheim an der Bergstrasse, Germany) 2010, 16, 13262 - 70.
Liang, H. ; Ciufolini, M. A. Progress Towards The Synthesis Of Sordarin And Its Analogs. Organic Preparations and Procedures International 2010, 42, 111 - 132.
Zhang, J. ; Coqueron, P. - Y. ; Vors, J. - P. ; Ciufolini, M. A. Synthesis Of 5-Amino-Oxazole-4-Carboxylates From Α-Chloroglycinates. Organic Letters 2010, 12, 3942 - 3945.
Liang, H. ; Ciufolini, M. A. Synthetic Aspects Of The Oxidative Amidation Of Phenols. Tetrahedron 2010, 66, 5884 - 5892.
Semple, S. C. ; Akinc, A. ; Sandhu, A. ; Mui, B. ; Chow, C. ; Sah, D. ; Stebbing, D. ; Crosley, E. ; Hafez, I. ; Dorkin, J. R. ; Qin, J. ; Lam, K. ; Wong, K. ; Nechev, L. ; Eisenhardt, M. L. ; Jayaraman, M. ; Kazem, M. ; Maier, M. ; Srinivasulu, M. ; Weinstein, M. ; Chen, Q. ; Alvarez, R. ; Barros, S. ; Klimuk, S. K. ; Borland, T. ; Kosovrasti, V. ; Tam, Y. ; MacLachlan, I. ; Manoharan, M. ; Ciufolini, M. A. ; Tracy, M. ; de Fougerolles, A. ; Cullis, P. R. ; Madden, T. D. ; Hope, M. J. Discovery Of Next-Generation Sirna Delivery Systems Through Rational Design Of Novel Cationic Lipids. In Nature Biotechnology; Nature Biotechnology; 2010; Vol. 28, pp. 172-U18.
Liang, H. ; Ciufolini, M. A. Tandem Phenolic Oxidative Amidation-Intramolecular Diels-Alder Reaction: An Approach To The Himandrine Core. Organic Letters 2010, 12, 1760 - 1763.

2009

Mendelsohn, B. A. ; Ciufolini, M. A. Approach To Tetrodotoxin Via The Oxidative Amidation Of A Phenol. Organic Letters 2009, 11, 4736-4739.
Patrick, B. O. ; Liang, H. ; Canesi, S. ; Ciufolini, M. A. 10-Ethynyl-2,3,6,6A,9,10-Hexahydro-1H-6,9-Methanopyrrolo[2,1-I][2,1]Benz Othiazol-10-Ol 5,5-Dioxide. Acta Crystallographica Section E-Structure Reports Online 2009, 65, O2621-U2491.
Chau, J. ; Zhang, J. M. ; Ciufolini, M. A. A Peterson Avenue To 5-Alkenyloxazoles. Tetrahedron Letters 2009, 50, 6163-6165.
Zhang, J. M. ; Ciufolini, M. A. Total Synthesis Of Siphonazoles By The Use Of A Conjunctive Oxazole Building Block. Organic Letters 2009, 11, 2389-2392.
Schule, A. ; Liang, H. ; Vors, J. P. ; Ciufolini, M. A. Synthetic Studies Toward Sordarin: Building Blocks For The Terpenoid Core And For Analogues Thereof. Journal of Organic Chemistry 2009, 74, 1587-1597.
Zhang, J. M. ; Polishchuk, E. A. ; Chen, J. ; Ciufolini, M. A. Development Of An Oxazole Conjunctive Reagent And Application To The Total Synthesis Of Siphonazoles. Journal of Organic Chemistry 2009, 74, 9140-9151.
Aulakh, V. S. ; Ciufolini, M. A. An Improved Synthesis Of Pyridine-Thiazole Cores Of Thiopeptide Antibiotics. Journal of Organic Chemistry 2009, 74, 5750-5753.
Mendelsohn, B. A. ; Lee, S. ; Kim, S. ; Teyssier, F. ; Aulakh, V. S. ; Ciufolini, M. A. Oxidation Of Oximes To Nitrile Oxides With Hypervalent Iodine Reagents. Organic Letters 2009, 11, 1539-1542.
Liang, H. ; Canesi, S. ; Patrick, B. O. ; Ciufolini, M. A. Crystal Structure Of 2,3,6A,9-Tetrahydro-1H-6,9-Methanopyrrolo[2,1-I][2,1]Benzisothiazol-10(6 H)-One 5,5-Dioxide, C11H13No3S. Zeitschrift Fur Kristallographie-New Crystal Structures 2009, 224, 83-84.
Lefranc, D. ; Ciufolini, M. A. Total Synthesis And Stereochemical Assignment Of Micrococcin P1. Angewandte Chemie-International Edition 2009, 48, 4198-4201.
Dubreuil, P. ; Letard, S. ; Ciufolini, M. ; Gros, L. ; Humbert, M. ; Casteran, N. ; Borge, L. ; Hajem, B. ; Lermet, A. ; Sippl, W. ; Voisset, E. ; Arock, M. ; Auclair, C. ; Leventhal, P. S. ; Mansfield, C. D. ; Moussy, A. ; Hermine, O. Masitinib (Ab1010), A Potent And Selective Tyrosine Kinase Inhibitor Targeting Kit. PLOS ONE 2009, 4, e7258.

2008

Liang, H. ; Ciufolini, M. A. Improved Procedure For The Bimolecular Oxidative Amidation Of Phenols. Journal of Organic Chemistry 2008, 73, 4299-4301.
Patrick, B. O. ; Mendelsohn, B. A. ; Ciufolini, M. A. Crystal Structure Of Methyl 2-(1-Acetamido-4-Oxocyclohexa-2,5-Dienyl)Acetate, C11H13No4. Zeitschrift Fur Kristallographie-New Crystal Structures 2008, 223, 205-206.
Patrick, B. O. ; Mendelsohn, B. A. ; Ciufolini, M. A. Crystal Structure Of N-((2Ar,2A(1)S,3S,5As,7R)-3,7-Dihydroxy-2A,2A(1),3,5A,6,7-Hexahydroinden O[1,7-Cd]Isoxazol-5A-Yl)Acetamide, C11H14N2O4. Zeitschrift Fur Kristallographie-New Crystal Structures 2008, 223, 203-204.

2007

Ciufolini, M. A. ; Chan, B. K. Methodology For The Synthesis Of Pyridines And Pyridones: Development And Applications. Heterocycles 2007, 74, 101-124.
Liang, H. ; Schule, A. ; Vors, J. P. ; Ciufolini, M. A. An Avenue To The Sordarin Core Adaptable To Analog Synthesis. Organic Letters 2007, 9, 4119-4122.
Chan, B. K. ; Ciufolini, M. A. Total Synthesis Of Streptonigrone. Journal of Organic Chemistry 2007, 72, 8489-8495.
Ciufolini, M. A. ; Braun, N. A. ; Canesi, S. ; Ousmer, M. ; Chang, J. ; Chai, D. Oxidative Amidation Of Phenols Through The Use Of Hypervalent Iodine Reagents: Development And Applications. Synthesis-Stuttgart 2007, 3759-3772.

2006

Tan, J. S. ; Ciufolini, M. A. Total Synthesis Of Topopyrones B And D. Organic Letters 2006, 8, 4771-4774.
Chang, J. J. ; Chan, B. ; Ciufolini, M. A. Synthetic Studies Toward Spiroleucettadine. Tetrahedron Letters 2006, 47, 3599-3601.
Ciufolini, M. A. ; Canesi, S. ; Ousmer, M. ; Braun, N. A. Synthetic Ventures Inspired By Biosynthetic Hypotheses: The Evolution Of A Method For The Oxidative Amidation Of Phenols. Tetrahedron 2006, 62, 5318-5337.
Vincent, G. ; Mansfield, D. J. ; Vors, J. P. ; Ciufolini, M. A. Studies Toward Soraphen A: An Aldol-Metathesis Avenue To The Macrocyclic Framework. Organic Letters 2006, 8, 2791-2794.

2005

Canesi, S. ; Bouchu, D. ; Ciufolini, M. A. Nitrogenous Educts Through Oxidative Amidation Of Phenols: The Bimolecular Reaction. Organic Letters 2005, 7, 175-177.