The synthesis of nonactic acid Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/js956j92t

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  • Alkylation of propylene oxide with 2-lithiofuran gave alcohol I, which was smoothly converted to acetylfuran II. hydrogenation of II over rhodium on charcoal followed by Jones' oxidation afforded ketone III. Further transformation into IV was accomplished via a Wittig reaction followed by saponification with methanolic sodium hydroxide. Hydroboration of the resulting olefin IV followed by oxidative work-up with Jones' reagent gave a 2:1 mixture of Va and Vb. Reduction of Vb with lithium tri-sec-butyl borohydride gave a 9:1 mixture of VIa and VII:). Hydroxyacid VIa was further transformed into benzoate VII by esterification followed by an inversion of configuration at C-8. Methanolysis of VII afforded methyl nonactate VIII.
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  • description.provenance : Approved for entry into archive by Deborah Campbell(deborah.campbell@oregonstate.edu) on 2013-11-20T18:02:00Z (GMT) No. of bitstreams: 1 ArcoManuel1976.pdf: 851637 bytes, checksum: 0a016f99455ca8cbed0c4baa4a7ead90 (MD5)
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  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2013-11-14T16:27:44Z (GMT) No. of bitstreams: 1 ArcoManuel1976.pdf: 851637 bytes, checksum: 0a016f99455ca8cbed0c4baa4a7ead90 (MD5)
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