biomimetic synthesis and structural revision of (+/-)-tridachiahydropyrone
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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 - PowerPoint PPT PresentationTRANSCRIPT
Biomimetic Synthesis and StructuralRevision 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
• 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
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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
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Woodward-Hoffman Rules
#e- Heat Light
4n Con Dis
4n+2 Dis Con
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Retrosynthesis
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Forward Synthesis
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• 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
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Questions
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