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- W58160802 abstract "An unexpected bicyclo[3.3.1]nonane ring system arising from the use of the popular oxidant 2- iodoxybenzoic acid (IBX), led to investigations into the previously undisclosed physical properties (acidity, proton affinity) of this reagent (Chapter 1). Resulting from a collaborative effort, discussions concern the pKa determination of IBX in aqueous and dimethylsulfoxide media; as well as computationally determined gas-phase proton affinity of IBX and its reduced form 2- iodosobenzoic acid (IBA). These results elaborate the quite significant acidic character of IBX and suggest future users of this compound should take care if acid sensitivity is a concern in their system. For our purposes, IBX complexed with N-methyl morpholine-N-oxide allowed access to the desired target. The unexpected bicyclo[3.3.1]nonane ring system arising from IBX oxidation, directed our focus toward a total synthesis campaign of the natural product spirovibsanin A (Chapter 2). Spirovibsanin A is a member of the rare vibsane natural product family, whose structures are characterised by polycyclic, polyoxygenated cores. Key to this synthetic endeavor was trapping the bicyclo[3.3.1]nonane ring system as a methyl ether in high yield. Similarly, a novel keto transposition/carbonylation sequence provided a functionalised advanced synthon from which subsequent synthesis could be envisioned. Crucial to the synthetic campaign was a one-pot osmium mediated dihydroxylation/lactonisation protocol which accessed a troublesome and congested spirolactone moiety in high yield. These synthetic efforts led to the total synthesis of 5,14-bis-epi- spirovibsanin A. Discussions consider the synthetic trials and tribulations that led to the bis-epimer of this natural product; as well as efforts to obtain the full natural product. In the future, this synthetic sequence should form the basis of a number of total synthesis campaigns of related vibsane family members." @default.
- W58160802 created "2016-06-24" @default.
- W58160802 creator A5080686275 @default.
- W58160802 date "2008-06-01" @default.
- W58160802 modified "2023-09-27" @default.
- W58160802 title "2-Iodoxybenzoic Acid: Acidity Investigations and The Total Synthesis of 5,14-bis-epi-Spirovibsanin A" @default.
- W58160802 hasPublicationYear "2008" @default.
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