John Porco
John Porco
Seminar
Thu, Mar. 10, 2016, 4:30pm
Frick Chemistry Laboratory, Taylor Auditorium
Host: Robert Knowles
Thu, Mar. 10, 2016, 4:30pm
Frick Chemistry Laboratory, Taylor Auditorium
Host: Robert Knowles
Recent Studies Towards The Synthesis of Tetrahydroxanthone Natural Products
A concise approach to additional tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums derived from chromones and a late-stage Dieckmann cyclization has also developed (1). The methodology led to development of efficient syntheses of the antitumor agents secalonic acids A and D (2) as well as a seven-step atropselective total synthesis of the dimeric tetrahydroxanthone antibiotic rugulotrosin A (3).
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(1) Vinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products. Qin, T.; Johnson, R. P.; and Porco, J.A. Jr. J. Am. Chem. Soc. 2011, 133, 1714–1717.
(2) Total Syntheses of Secalonic Acids A and D. Qin, T.; Porco, J.A. Jr. Angew. Chem. Int. Ed. Engl., 2014, 53, 3107-3110.
(3) Atropselective Syntheses of (-) and (+) Rugulotrosin A Utilizing Point-to-Axial Chirality Transfer. Qin, T.; Skraba-Joiner, S.L.; Khalil, Z.G.; Johnson, R.P.; Capon, R.J.; Porco J.A, Jr.
Nat. Chem. 2015, 7, 234-40.