1. Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone P. Sharma, N. Gri ffi ths, J. E. Moses, Org. Lett. 2008, 10, 4025 – 4027 Present By Andrew Blemings

2. Dr. John E. Moses Master University of Bath, 2001, under Ian Rothwell PhD from University of Oxford, 2004, under Jack Baldwin Went to Scripps in 2004 Went to University of London in 2005 Appointed Associate Professor in 2007 Promoted to Reader of Chemical Biology in 2011 26 publications 1

3. Tridachiahydropyrones First isolated in 1996 by Cimino from mollusks Although synthesized by Jeffrey of Flinders in 2005, NMR did not match natural product Moses hoped to use Biomimetic chemistry to find the natural product Tridachiahydropyrones are used by mollusks to protect themselves from UV light Believed to occur via a 6 π electrocyclization from UV light –A thermal electrocyclization would produce the trans product –A light induced cyclization produces the cis product which matches the natural product 2

4. Woodward-Hoffman Rules #e-HeatLight 4nConDis 4n+2DisCon 3

5. Retrosynthesis 4

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8. Forward Synthesis 7

9. Ran last step in MeOH, hv, for 60hrs –Isolated the cis isomer in 29% yield Ran the last step again in xylene at 150°C –Yielded no product 8

10. Questions 9