Research Publications

2003 – 2013

[56] Lisboa, M. P.; Dudley, G. B. Synthesis of cytotoxic palmerolides. Chem.–Eur. J. 2013, 19, 16146-16168.

[55] Hoang, T. T.; Dudley, G. B. Synthesis of high-value 1,6-enynes by tandem fragmentation/olefination. Org. Lett. 2013, 15, 4026-4029.

[54] Dudley, G. B.; Stiegman, A. E.; Rosana, M. R. Correspondence on microwave effects in organic synthesis. Angew. Chem. Int. Ed. 2013, 52, 7918-7923.

[53] Lisboa, M. P.; Jones, D. M.; Dudley, G. B. Formal synthesis of palmerolide A, featuring alkynogenic fragmentation and syn-selective vinylogous aldol chemistry. Org. Lett. 2013, 15, 886-889.

[52] Gold, B.; Dudley, G. B.; Alabugin, I. V. Moderating strain without sacrificing reactivity: Design of fast and tunable noncatalyzed alkyne-azide cycloadditions via stereoelectronically controlled transition state stabilization. J. Am. Chem. Soc. 2013, 135, 1559-1569.

[51] Tummatorn, J.; Diaz Muñoz, G.; Dudley, G. B. Synthesis of (–)-(R)-angustureine by formal alkynylation of a chiral ß-amino ester. Tetrahedron Lett. 2013, 54, 1312-1314.

[50] Tlais, S. F.; Dudley, G. B. On the proposed structures and stereocontrolled synthesis of the cephalosporolides. Beilstein J. Org. Chem. 2012, 8, 1287-1292.

[49] Yang, J.; Wangweerawong, A.; Dudley, G. B. [1,2]-Wittig rearrangement of aromatic heterocycles. Heterocycles 2012, 85, 1603-1606.

[48] Batsomboon, P.; Gold, B. A.; Alabugin, I. V.; Dudley, G. B. Tandem nucleophilic addition/fragmentation of vinylogous acyl nonaflates for the synthesis of functionalized alkynes, with new mechanistic insight. Synthesis 2012, 44, 1818-1824. (Special Topic Issue: Tandem Reactions)

[47] Lisboa, M. P.; Jeong-Im, J. H.; Jones, D. M.; Dudley, G. B. Toward a new palmerolide assembly strategy: synthesis of C16–C24. Synlett 2012, 23, 1493-1496.

[46] Tummatorn, J.; Batsomboon, P.; Clark, R. J.; Alabugin, I. V.; Dudley, G. B. Strain-promoted azide–alkyne cycloadditions of benzocyclononynone. J. Org. Chem. 2012, 77, 2093-2097.

[45] Rosana, M. R.; Tao, Y.; Stiegman, A. E.; Dudley, G. B. On the rational design of microwave-actuated organic reactions.
Chem. Sci. 2012, 3, 1240-1244. Featured in Chemistry World and Chemical and Engineering News

[44] Gold, B.; Shevchenko, N. E.; Bonus, N.; Dudley, G. B.; Alabugin, I. V. Selective transition state stabilization via hyperconjugative assistance: stereoelectronic concept for copper-free click chemistry. J. Org. Chem. 2012, 77, 75-89.

[43] Wang, T.; Intaranukulkit; T.; Rosana, M. R.; Slegeris, R.; Simon, J.; Dudley, G. B. Microwave-assisted benzyl-transfer reactions of commercially available 2-benzyloxy-1-methylpyridinium triflate. Org. Biomol. Chem. 2012, 10, 248-250.

[42] Lisboa, M. P.; Hoang, T. T.; Dudley, G. B. Tandem nucleophilic addition / fragmentation of vinylogous acyl triflates: 2-methyl-2-(1-oxo-5-heptynyl)-1,3-dithiane. Org. Synth. 2011, 88, 353-363.

[41] Yang, J.; Tummatorn, J.; Slegeris, R.; Tlais, S. F.; Dudley, G. B. Synthesis of the tricyclic core of aldingenin B by oxidative cyclo-ketalization of an alkyne-diol. Org. Lett. 2011, 13, 2065-2067.

[40] Tlais, S. F.; Dudley, G. B. A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals. Beilstein J. Org. Chem. 2011, 7, 570-577.

[39] Tummatorn, J.; Dudley, G. B. Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates. Org. Lett. 2011, 13, 1572-1575.

[38] Tummatorn, J.; Dudley, G. B. Stereodefined homopropargyl amines by tandem nucleophilic addition / fragmentation of dihydropyridone triflates. Org. Lett. 2011, 13, 158-160.

[37] Yang, J.; Dudley, G. B. Pyridine-directed organolithium addition to an enol ether. Adv. Synth. Catal. 2010, 352, 3438-3442.

[36] Tlais, S. F.; Dudley, G. B. Stereocontrol of 5,5-spiroketals in the synthesis of cephalosporolide H epimers. Org. Lett. 2010, 12, 4689-4701.

[35] Jones, D. M.; Dudley, G. B. An open-and-shut strategy: preparation of benzo-fused indanes by ring-opening of a vinylogous acyl triflate and metal-catalyzed Asao–Yamamoto benzannulation. Tetrahedron 2010, 66, 4860-4866. (Special Issue)

[34] Jones, D. M.; Lisboa, M. P.; Kamijo, S.; Dudley, G. B. Ring opening of cyclic vinylogous acyl triflates using stabilized carbanion nucleophiles: Claisen condensations linked to carbon–carbon bond cleavage. J. Org. Chem. 2010, 75, 3260-3267.

[33] Albiniak, P. A.; Dudley, G. B. New reagents for the synthesis of arylmethyl ethers and esters. Synlett 2010, 841-851. (Account)

[32] Jones, D. M.; Dudley, G. B. Synthesis of the C1–C15 region of palmerolide A using refined Claisen-type addition / bond cleavage methodology. Synlett 2010, 223-226.

[31] Tlais, S. F.; Clark, R. J.; Dudley, G. B. A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis. Molecules 2009, 14, 5216-5222. (Open Access)

[30] Yang, J.; Dudley, G. B. [1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers. J. Org. Chem. 2009, 74, 7998-8000.

[29] Engel, D. A.; Dudley, G. B. The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds. Org. Biomol. Chem. 2009, 7, 4149-4158. (invited Perspective Article)

[28] Tlais, S. F.; Lam, H.; House, S. E.; Dudley, G. B. New strategies for protecting group chemistry: synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl (PSB) ethers. J. Org. Chem. 2009, 74, 1876-1885.

[27] Lopez, S. S.; Dudley, G. B. Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine. Beilstein J. Org. Chem. 2008, 4, No 44; doi:10.3762/bjoc.4.44. (Open Access)

[26] Tummatorn, J.; Dudley, G. B. Ring-opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols. J. Am. Chem. Soc. 2008, 130, 5050-5051.

[25] Kozytska, M. V.; Dudley, G. B. On the intramolecular pyrone Diels-Alder approach to basiliolide B. Tetrahedron Lett. 2008, 49, 2899-2901.

[24] Engel, D. A.; Lopez, S. S.; Dudley, G. B. Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones. Tetrahedron 2008, 64, 6988-6996. (Special Issue)

[23] Albiniak, P. A.; Amisial, S. M.; Dudley, G. B.; Hernandez, J. P.; House, S. E.; Matthews, M. E.; Nwoye, E. O.; Reilly, M. K.; Tlais, S. F. Stable oxypyridinium triflate (OPT) salts for the synthesis of halobenzyl ethers. Synth. Commun. 2008, 38, 656-665. (Dedicated to Prof Ken Goldsby for his support of undergraduate research at FSU.)

[22] Tummatorn, J.; Albiniak, P. A.; Dudley, G. B. Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate. J. Org. Chem. 2007, 72, 8962-8964.

[21] Albiniak, P. A.; Dudley, G. B. Thermally generated phenylcarbenium ions: acid-free and self-quenching Friedel-Crafts reactions. Tetrahedron Lett. 2007, 48, 8097-8100.

[20] Yang, J.; Dudley, G. B. Conjugate addition of organocopper reagents in dichloromethane to alpha,beta-unsaturated esters. Tetrahedron Lett. 2007, 48, 7887-7889.

[19] Dudley, G. B.; Engel, D. A.; Lam, H.; Poon, K. W. C.; Singletary, J. A. Synthesis of dihydro-epi-deoxyarteannuin B. Org. Lett. 2007, 9, 2839-2842.

[18] Poon, K. W. C.; Albiniak, P. A.; Dudley, G. B. Protection of alcohols using 2-benzyloxy-1-methylpyridinium trifluoromethanesulfonate: methyl (R)-(-)-3-benzyloxy-2-methyl propanoate. Org. Synth. 2007, 84, 295-305.

[17] Lopez, S. S.; Engel, D. A.; Dudley, G. B. The Meyer-Schuster rearrangement of ethoxyalkynyl carbinols. Synlett 2007, 949-953.

[16] Nwoye, E. O.; Dudley, G. B. A method for the synthesis of para-methoxybenzyl (PMB) ethers under effectively neutral conditions. Chem. Commun. 2007, 1436-1437.

[15] Engel, D. A.; Dudley, G. B. Olefination of Ketones Using A Gold(III)-Catalyzed Meyer-Schuster Rearrangement. Org. Lett. 2006, 8, 4027-4029.

[14] Kamijo, S.; Dudley, G. B. Cyclic Vinylogous Triflate Hemiacetals as New Surrogates for Alkynyl Aldehydes. Tetrahedron Lett. 2006, 47, 5629-5632.

[13] Kamijo, S.; Dudley, G. B. Tandem Nucleophilic Addition/Fragmentation Reactions and Synthetic Versatility of Vinylogous Acyl Triflates. J. Am. Chem. Soc. 2006, 128, 6499-6507.

[12] Poon, K. W. C.; Dudley, G. B. Mix-and-Heat Benzylation of Alcohols using a Bench-Stable Pyridinium Salt. J. Org. Chem. 2006, 71, 3923-3927.

[11] Jones, D. M.; Kamijo, S.; Dudley, G. B. Grignard-Triggered Fragmentation of Vinylogous Acyl Triflates: Synthesis of (Z)-6-Heneicosen-11-one, the Douglas Fir Tussock Moth Sex Pheromone. Synlett 2006, 936-938.

[10] House, S. E.; Poon, K. W. C.; Lam, H.; Dudley, G. B. p-Siletanylbenzylidene Acetal: Oxidizable Protecting Group for Diols. J. Org. Chem. 2006, 71, 420-422.

[9] Kamijo, S.; Dudley, G. B. Claisen-Type Condensation of Vinylogous Acyl Triflates. Org. Lett. 2006, 8, 175-177.

[8] Poon, K. W. C.; House, S. E.; Dudley, G. B. A Bench-Stable Organic Salt for Benzylation of Alcohols. Synlett 2005, 3142-3144.

[7] Briggs, T. F.; Dudley, G. B. Synthesis of the Floresolide B Hydroquinone Lactone Core using Ring-Closing Metathesis. Tetrahedron Lett. 2005, 46, 7793-7796.

[6] Salamone, S. G.; Dudley, G. B. A Ring Expansion Approach to Roseophilin. Org. Lett. 2005, 7, 4443-4445.

[5] Kozytska, M. V.; Dudley, G. B. Siletanylmethyllithium: An Ambiphilic Organosilane. Chem. Commun. 2005, 3047-3049.

[4] Lam, H.; House, S. E.; Dudley, G. B. The para-Siletanylbenzyl (PSB) Ether: A Peroxide-Cleavable Protecting Group for Alcohols and Phenols. Tetrahedron Lett. 2005, 46, 3283-3285.

[3] Kamijo, S.; Dudley, G. B. A Tandem Carbanion Addition/Carbon-Carbon Bond Cleavage Yields Alkynyl Ketones. J. Am. Chem. Soc. 2005, 127, 5028-5029.

[2] Singletary, J. A.; Lam, H.; Dudley, G. B. A Succinct Method for Preparing the Stork-Jung Vinylsilane Robinson Annulation Reagent. J. Org. Chem. 2005, 70, 739-741.

[1] Sunderhaus, J. D.; Lam, H.; Dudley, G. B. Oxidation of Carbon-Silicon Bonds: The Dramatic Advantage of Strained Siletanes. Org. Lett. 2003, 5, 4571-4573.