Gretchen Peters
February 10, 2011
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Total synthesis and chemical biology
Focus of syntheses: “naturally occurring
complex molecules that challenge the stateof-the-art of organic synthesis”
Complexes that are unique structurally and
biologically
http://www.chem.harvard.edu/research/faculty/
matthew_shair/research/research.html
(-)-himeradine A
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lycodine
(+)-fastigiatine
Found in plants (clubmosses)
Members have been found to have
cardiovascular and neuromuscular effects
Used for homeopathic remedies
http://findarticles.com/p/articles/mi_g26
03/is_0004/ai_2603000497/
1,4 Addition
Mannich
Condensation
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7
Wanted to remove
protecting group and
induce addition
Free amine too reactive
Added on to a,b
unsaturated ketone to
form five-membered
ring
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First synthesis of (+)-fastigiatine
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15 step synthesis with 30% overall yield
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Chem 647 classmates
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Dr. Davis