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The Micalizio Lab

55. V. Jeso, C. Yang, M. D. Cameron, J. L. Cleveland, G. C. Micalizio “Synthesis and Structure–Activity Relationships of Lehualide B – A Marine-derived Natural Product with Potent Anti-Multiple Myeloma Activity” ACS Chemical Biology, 2013, 8, accepted.
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54. V. Jeso, S. Iqbal, P. Hernandez, M. D. Cameron, P. V. LoGrasso, G. C. Micalizio “Synthesis of Benzoquinone Ansamycin-Inspired Macrocyclic Lactams from Shikimic Acid” Angew. Chem. Int. Ed. 2013, 52, accepted.
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53. V. Jeso, G. C. Micalizio “Relay catalysis at a boron centre” Nature (News and Views) 2013, 494, 179-181.
52. D. Yang, G. C. Micalizio, “Synthesis of Alkaloid (–)-205B via Stereoselective Reductive Cross-Coupling and Intramole98cular [3+2] Cycloaddition” J. Am. Chem. Soc., 2012, 134, 15237-15240.
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51. P. S. Diez, G. C. Micalizio, “Convergent Synthesis of Deoxypropionates” Angew. Chem. Int. Ed., 2012, 51, 5152-5156.
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50. O. Kubo, D. P. Canterbury, G. C. Micalizio "Synthesis of the C1-C26 Hexacyclic Subunit of Pectenotoxin 2" Org. Lett., 2012, accepted (DOI:10.1021/ol302751b).
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49. S. Greszler, H. A. Reichard, G. C. Micalizio, "Asymmetric Synthesis of Dihydroindanes by Convergent Alkoxide-Directed Metallacycle-Mediated Bond Formation" J. Am. Chem. Soc. 2012, 134, 2766-2774.
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48. M. Z. Chen, G. C. Micalizio "Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines" J. Am. Chem. Soc. 2012, 134, 1352-1356.
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47. C. Aquino, M. Sarkar, M. J. Chalmers, K. Mendez, T. Kodadek, G. C. Micalizio "A Biomimetic Polyketide-Inspired Approach to Small Molecule Ligand Discovery" Nature Chem. 2012, 4, 99-104.
46. V. Jeso, L. Cherry, T. K. Macklin, S. C. Pan, P. V. LoGrasso, G. C. Micalizio "Convergent Synthesis and Discovery of a Natural Product-Inspired Paralog-Selective Hsp90 Inhibitor" Org. Lett. 2011, 13, 5108-5111.
45. D. Yang, G. C. Micalizio, "Convergent and Stereodivergent Synthesis of Complex 1-Aza-7-Oxabicyclo[2.2.1]heptanes" J. Am. Chem. Soc. 2011, 133, 9216-9219.
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44. D. P. Canterbury, G. C. Micalizio, "Convergent Route to the CDEF Tetracycle of Pectenotoxin-2" Org. Lett. 2011, 13, 2384-2387.
43. M. A. Tarselli, K. M. Raehal, A. K. Brasher, C. Groer, M. D. Cameron, L. M. Bohn, G. C. Micalizio, "Synthesis of Conolidine and Discovery of a Novel Analgesic for Chronic and Persistent Pain" Nature Chem. 2011, 3, 449-453.
42. D. Yang, J. K. Belardi, G. C. Micalizio, "Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions" Invited Article for a special issue in honor of Professor Harry Wasserman, Tetrahedron Lett. 2011, 52, 2144-2147.
41. H. A. Reichard, G. C. Micalizio, "Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes" Invited Perspective Article, Chem. Sci. 2011, 2, 573-589.
40. M. Z. Chen, M. McLaughlin, M. Takahashi, M. A. Tarselli, D. Yang, S. Umemura, G. C. Micalizio, "Preparation of Stereodefined Homoallylic Amines from the Reductive Cross-Coupling of Allylic Alcohols with Imines" J. Org. Chem., 2010, 75, 8048-8059.
39. V. Jeso, G. C. Micalizio, "Total Synthesis of Lehualide B by Allylic Alcohol–Alkyne Reductive Cross-Coupling" J. Am. Chem. Soc. 2010, 132, 11422-11424.
38. Diez, P.S.; Micalizio, G.C. "Chemoselective Reductive Cross-Coupling of 1,5-Dien-3-ols with Alkynes: A Facile Entry to Stereodefined Skipped Trienes" J. Am. Chem. Soc. 2010, 132, 9576–9578
37. D. P. Canterbury, G. C. Micalizio, "Polyketide Assembly by Alkene–Alkyne Reductive Cross-Coupling: Spiroketals Through the Union of Homoallylic Alcohols" J. Am. Chem. Soc. 2010, 132, 7602-7604.
36. T. K. Macklin, G. C. Micalizio, "Convergent and Stereospecific Synthesis of Skipped Polyenes and Polyunsaturated Fatty Acids" Nature Chem. 2010, 2, 638-643.
35. M. Takahashi, G. C. Micalizio, "Concerning the Potential Reversibility of Carbometalation in Akoxide-directed Ti(Oi-Pr)4-mediated Reductive Cross-Coupling of Homoallylic Alcohols with Aromatic Imines" Chem. Commun. 2010, 46, 3336-3338.
34. A. U. Barlan, G. C. Micalizio, "The Regio- and Stereochemical Course of Reductive Cross-Coupling Reactions Between 1,3-Disubstituted Allenes and Vinylsilanes: Synthesis of Z-Dienes" Tetrahedron, Symposium-in-Print honoring Brian Stoltz for his receipt of the Tetrahedron Young Investigator Award, 2010, 66, 4775-4783.
33. H. A. Reichard, M. McLaughlin, M. Z. Chen, G. C. Micalizio "Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes" Eur. J. Org. Chem. 2010, 391-409.
32. D. Yang, G. G. Micalizio "A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-Hydroxymethyl Substituted Allylic Silanes with Imines" J. Am. Chem. Soc. 2009, 131, 17548-17549.
31. S. Umemura, M. McLaughlin, G. C. Micalizio "Convergent Synthesis of Stereodefined Exo-alkylidene–γ–Lactams from β-Halo Allylic Alcohols" Org. Lett. 2009, 11, 5402-5405.
30 M. Z. Chen, G. C. Micalizio "A Two-Step, Three-Component Coupling Process for the Synthesis of Highly Substituted Piperidines: Exploring the Utility of a Unique Regioselective Cross-Coupling Reaction of Conjugated Alkynes" Org. Lett. 2009, 11, 4982-4985.
29. M. A. Tarselli, G. C. Micalizio "Aliphatic Imines in Titanium-Mediated Reductive Cross-Coupling: Unique Reactivity of Ti(Oi-Pr)4/n-BuLi" Org. Lett. 2009, 11, 4596-4599.
28. L. J. Perez, H. L. Shimp, G. C. Micalizio "Stereoselective Synthesis of Trisubstituted (E,E)-1,3-Dienes by the Site-Selective Reductive Cross-Coupling of Internal Alkynes with Terminal Alkynes: A New Fragment Coupling Reaction for Natural Product Synthesis" J. Org. Chem. – Featured Article, 2009, 74, 7211-7219.
27. H. L. Shimp, G. C. Micalizio "A Formal Total Synthesis of Dictyostatin" Tetrahedron, 2009, 65, 5908-5915.
26. M. Takahashi, M. McLaughlin, G. C. Micalizio "Complex Allylation by the Direct Cross-Coupling of Imines with Unactivated Allylic Alcohols" Angew. Chem. Int. Ed. 2009, 48, 3648-3652.
25. T. K. Macklin, G. C. Micalizio "Total Synthesis and Structure Elucidation of (+)-Phorbasin C" J. Am. Chem. Soc. 2009, 131, 1392-1393.
24. J. K. Belardi, G. C. Micalizio "Conversion of Allylic Alcohols to Stereodefined Trisubstituted Alkenes: A Complimentary Process to the Claisen Rearrangement" J. Am. Chem. Soc. 2008, 130, 16870-16872.
23. H. A. Reichard, J. C. Rieger, G. C. Micalizio, "Total Synthesis of Callystatin A by Titanium-mediated Reductive Alkyne–Alkyne Cross-Coupling" Angew. Chem. Int. Ed. 2008, 47, 7837-7840.
22. J. K. Belardi, G. C. Micalizio, "Total Synthesis of Macbecin I" Angew. Chem. Int. Ed. 2008, 47, 4005-4008.
21. M. McLaughlin, H. L. Shimp, R. Navarro, G. C. Micalizio "Regio- and Stereoselective Direct Cross-Coupling of Imines with Allenic Alcohols" (invited Cluster Article by Hisashi Yamamoto) Synlett 2008, 735-738.
20. H. L. Shimp, A. Hare, M. McLaughlin, G. C. Micalizio, "Allene-Alkyne Cross-Coupling for Stereoselective Synthesis of Substituted 1,4-Dienes and Cross-Conjugated Trienes" (invited for Symposium-in-Print honoring John Hartwig for his receipt of the Tetrahedron Prize) Tetrahedron 2008, 64, 3437-3445.
19. L. Perez, G. C. Micalizio "Titanium-Mediated Fragment Union Processes in Complex Molecule Synthesis: Development of a Branched Reaction Pathway of High Step Economy for the Synthesis of Complex and Diverse Polyketides" (invited Feature Article) 2008, 627-648.
18.
F. Kolundzic, G.C. Micalizio, "Allylic Alkylation of Unactivated Allylic Alcohols via Formal Metallo-[3,3]-Rearrangement" J. Am. Chem. Soc. 2007, 129, 15112-15113.
17.
H.L. Shimp, G.C. Micalizio, "An Alkoxide-Directed Alkyne-Allene Cross-Coupling for Stereoselective Synthesis of 1,4-Dienes" Chem. Commun. 2007, 4531-4533.
16.
M. Takahashi, G.C. Micalizio, "Regio- and Stereoselective Cross Coupling of Substituted Olefins and Imines. A Convergent Stereoselective Synthesis of Saturated 1,5-Aminoalcohols and Substituted Piperidines" J. Am. Chem. Soc. 2007, 129, 7514-7516.
15.
M. McLaughlin, M. Takahashi, G.C. Micalizio, "An Alkoxide Directed Intermolecular [2+2+1] Annulation: A Three-Component Coupling Reaction for the Synthesis of Tetrasubstituted α,β-Unsaturated γ-Lactams" Angew. Chem. Int. Ed. 2007, 46, 3912-3914.
14.
H.A. Reichard, G.C. Micalizio, "A Site- and Stereoselective Intermolecular Alkene-Alkyne Coupling Process" Angew. Chem. Int. Ed. 2007, 46, 1440-1443.
13.
J.K. Belardi, G.C. Micalizio, "Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5) - C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A" Org. Lett. 2006, 8, 2409-2412.
12.
J. Ryan, G.C. Micalizio, "An Alkoxide-Directed Carbometalation of Internal Alkynes" J. Am. Chem. Soc. 2006, 128, 2764-2765.
11.
A.B. Bahadoor, G.C. Micalizio, "Studies in Macrolide Antibiotic Synthesis: The Role of Tethered Alkoxides in Titanium Alkoxide-Mediated Regioselective Reductive Coupling Reactions" Org. Lett. 2006, 8, 1181-1184.
10.
H.L. Shimp, G.C. Micalizio, "Group 4 Metals in Polyketide Synthesis: A Convergent Strategy for the Synthesis of Polypropionate-derived (E,E)-Trisubstituted 1,3-Dienes" Org. Lett. 2005, 7, 5111-5114.
9.
 A.B. Bahadoor, A. Flyer, G.C. Micalizio, "A Pentenyl Dianion-Based Strategy for Convergent Synthesis of Ene-1,5-diols" J. Am. Chem. Soc. 2005, 127, 3694-3695.
8.
J.-N. Heo, G. C. Micalizio, W. R. Roush, "Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring Closing Metathesis Reactions" Org. Lett. 2003, 5, 1693.
7.
G. C. Micalizio, S. L. Schreiber, "An Alkynylboronic Ester Annulation: Development of Synthetic Methods For Application to Diversity-Oriented Organic Synthesis" Angew. Chem. Int. Ed. 2002, 41, 3272.
6.
G. C. Micalizio and S. L. Schreiber, "A Boronic Ester Annulation Strategy for Diversity-Oriented Organic Synthesis" Angew. Chem. Int. Ed. 2002, 41, 152.
5.
G. C. Micalizio and W. R. Roush, "Studies on the Synthesis of Pectenotoxin II: Synthesis of a C(11)-C(26) Fragment Precursor via [3+2]-Annulation Reactions of Chiral Allylsilanes" Org. Lett. 2001, 3, 1949.
4.
W. R. Roush, A. N. Pinchuk, G. C. Micalizio, "[(E)-γ-(Dimethylphenylsilyl)-allyl]diisopinocampheylborane: A Highly Enantioselective Reagent for the Synthesis of anti-β-hydroxyallylsilanes" Tetrahedron Lett. 2000, 41, 9413.
3.
G. C. Micalizio, W. R. Roush, and A. N. Pinchuk, "Synthesis of the C(29)-C(45) E-F Bis-Pyran Subunit of Spongistatin 1 (Altohyrtin A)" J. Org. Chem. 2000, 65, 8730.
2.
G. C. Micalizio and W. R. Roush, "A Three-Component Coupling Strategy for Tetrahydrofuran Synthesis: Application of the Diisopropyl Tartrate Modified (E)-γ-(Dimethylphenylsilyl)allylboronate as an α,γ-Allyl Dianion Equivalent" Org. Lett. 2000, 2, 461.
1.
G. C. Micalizio and W. R. Roush, "Towards the Synthesis of Spongistatin 1: Diastereoselective Synthesis of the C(36)-C(45) Subunit" Tetrahedron Lett. 1999, 40, 3351.

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