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Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone

Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone. P. Sharma, N. Griffiths, J. E. Moses, Org. Lett. 2008, 10, 4025 – 4027 Present By Andrew Blemings. Dr. John E. Moses. Master University of Bath, 2001, under Ian Rothwell

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Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone

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  1. Biomimetic Synthesis and StructuralRevision of (+/-)-Tridachiahydropyrone P. Sharma, N. Griffiths, 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

  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 6π 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

  4. Woodward-Hoffman Rules

  5. Retrosynthesis

  6. Forward Synthesis

  7. 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. Questions

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