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Leo A. Paquette
Leo Paquette received his B.S. from Holy Cross College in 1956. He gothis Ph.D. from MIT in 1959. Professor Paquette is a Distinguished University Professor.
Natural Products, Organic Synthesis, Organic Methodology, Organometallics, Heterocyclic Chemistry
My research interests include the synthesis of structurally unique bioactivenatural products, the development of new methods particularlyenantioselective and asymmetric transformations, the identification of newthrusts involving biochemical probes and sensors, and broad investigation ofthe use of organometallic reagents for the expedient preparation of organiccompounds. Our current work aimed at the synthesis of spongistatin 1 (Figure1), pectenotoxin 2 (Figure 2), and amphidinol 3 (Figure 3) typifies ouractivity in the first category.
Our discovery of a general approach to the construction of inositol-basedmetal-ion ligating systems such as that shown in Figure 4 has led to manyexciting applications of this chemistry in bio-organic contexts. The abilityof these molecules to chelate metal ions selectively is expected to satisfythe increasing demands of modern medicine for sophisticated detectionmethods.
My group is also concerned with defining new aspects of organometallicapplications to synthesis. The zirconocene-promoted enantiospecific ringcontraction of carbohydrate precursors (Figure 5) represents an example ofour involvement with this chemistry. Our quest of pestalotiopsin A (Figure6) and fomannosin (Figure 7) involve the adoption of this ring contraction asa key transformation.
Peng, Xiaowen; Bondar, Dmitriy; Paquette, Leo A.. Alkoxide precoordination to rhodium enables stereodirected catalytic hydrogenation of a dihydrofuranol precursor of the C29-40 F/G sector of pectenotoxin-2. Tetrahedron (2004), 60(43), 9589-9598.
Paquette, Leo A.; Chang, Jiyoung; Liu, Zuosheng. Synthetic Studies Aimed at (-)-Cochleamycin A. Evaluation of Late-Stage Macrocyclization Alternatives. Journal of Organic Chemistry (2004), 69(19), 6441-6448.
Paquette, Leo A.; Barton, William R. S.; Gallucci, Judith C. Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO2-N Bond Cleavage. Organic Letters (2004), 6(8), 1313-1315.
Paquette, Leo A.; Hartung, Ryan E.; Hofferberth, John E.; Gallucci, Judith C. Reactions of a,a'-Dihydroxy Ketones with Phosgene. Structural Requirements for Spiro Epoxy Carbonate Formation. Organic Letters (2004), 6(6), 969-971.
Paquette, Leo A.. Spirocyclic Restriction of Nucleosides. Australian Journal of Chemistry (2004), 57(1), 7-17.
Paquette, Leo A.; Hong, Fang-Tsao. Total Synthesis of Dumsin. 1. Retrosynthetic Strategy and the Elaboration of Key Intermediates from (-)-Bornyl Acetate. Journal of Organic Chemistry (2003), 68(18), 6905-6918.
Paquette, Leo A.; Guevel, Ronan; Sakamoto, Shuichi; Kim, In Ho; Crawford, Jason. Convergent Enantioselective Synthesis of Vinigrol, an Architecturally Novel Diterpenoid with Potent Platelet Aggregation Inhibitory and Antihypertensive Properties. 1. Application of Anionic Sigmatropy to Construction of the Octalin Substructure. Journal of Organic Chemistry (2003), 68(16), 6096-6107.
Paquette, Leo A.. Fundamental mechanistic characteristics and synthetic applications of allylations promoted by indium metal in aqueous media. Synthesis (2003), (5), 765-774.
Yang, Jiong; Long, Yun Oliver; Paquette, Leo A.. Concise Total Syntheses of the Bioactive Mesotricyclic Diterpenoids Jatrophatrione and Citlalitrione. Journal of the American Chemical Society (2003), 125(6), 1567-1574.
Paquette, Leo A.; Kim, In Ho; Cuniere, Nicolas. Zirconocene-Mediated Route to Enantiopure 9-Oxabicyclononanes Functionalized on Both Carbon Bridges. Organic Letters (2003), 5(2), 221-223.