Synthetic studies of nonadrides Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/v405sd254

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  • An asymmetric approach to the synthesis of byssochlamic acid (1) is described. Regioisomeric enzymatic differentiation is described in the selective hydrolysis of dimethyl ester 30 by porcine liver esterase. Chiral dimethyl ester 42 was prepared by desymmetrization of cyclopentene 34 using porcine liver esterase. A key intramolecular [2+2]cycloaddition-cycloreversion photometathesis of diolide 69 was unsuccessful. An advanced intermediate 77 along an alternate route to 1 was synthesized. A synthetic route to bromoenone 164 has been completed. Compound 164 was utilized in a model study for a vinyl radical cyclization approach to the bicyclic core of CP-225,917 (8) and CP-263,114 (9). The strategy employs Birch reduction of o-anisaldehyde derivative 152 and elaboration of the side chain to provide an efficient route to 164. Initial attempts at cyclization to bicyclo[4.3.1]dec-1-ene 165 using tributyltin hydride and 2,2'-azobisisobutyronitrile (AIBN) were carried out, but no desired product was isolated under these conditions.
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