Title
An Enantioselective Synthesis of (-)-Coniine
Document Type
Article
Publication Date
2009
Abstract
Enantioselective syntheses have become increasingly important since the FDA declared enantiomers as separate chemical entities in the late nineties. (-)-coniine, a natural product derived from spotted Hemlock is responsible for killing Socrates in 399 B.C. Our synthesis begins by treating trans-2-hexenal with ethereal HCN in the presence of the enzyme oxynitrilase. Oxynitrilase is an enzyme isolated from consumer grade raw almonds. The cyano and hydroxy moieties then undergo an ethyl esterification and ethoxy carbonylation respectively. The resulting product is then reacted with Pd0 and an unsaturated sulfonamide which transposes the stereocenter and shifts the α,β-double bond into conjugation with the ester. Further manipulation of the palladium adduct affords the title compound, (-)-coniine.
Recommended Citation
Paulsen, Mark, "An Enantioselective Synthesis of (-)-Coniine" (2009). URC Student Scholarship.
http://scholar.oxy.edu/urc_student/293
Advisor
Don Deardorff
Department
chem
Support
Arnold and Mabel Beckman Foundation Scholars Award
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