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. / Graduation date: 1999
| Identifer | oai:union.ndltd.org:ORGSU/oai:ir.library.oregonstate.edu:1957/33377 |
| Date | 14 August 1998 |
| Creators | Drapela, Nicholas Ernest |
| Contributors | White, James D. |
| Source Sets | Oregon State University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis/Dissertation |
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