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  • Open Daily: 10am - 10pm
    Alley-side Pickup: 10am - 7pm

    3038 Hennepin Ave Minneapolis, MN
    612-822-4611

Open Daily: 10am - 10pm | Alley-side Pickup: 10am - 7pm
3038 Hennepin Ave Minneapolis, MN
612-822-4611
Discovery and Investigation of Trialkylborane/Water Mediated Radical Reactions, And, an Enantioselective Approach to the Securinega Alkaloids: The Tot

Discovery and Investigation of Trialkylborane/Water Mediated Radical Reactions, And, an Enantioselective Approach to the Securinega Alkaloids: The Tot

Medeiros, Matthew Richard

Paperback

Chemistry

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ISBN10: 1243789638
ISBN13: 9781243789631
Publisher: Proquest Umi Dissertation Pub
Pages: 200
Weight: 0.81
Height: 0.42 Width: 7.44 Depth: 9.69
Language: English
During the course of a total synthesis of phomoidride D, a deoxygenation reaction employing trimethylborane was observed. The absence of an obvious hydrogen atom source in the reaction prompted a deuterium study, which suggested the source of hydrogen atom was water. Experimental and computational studies supported the existence of a Me3B/water complex that was acting as the hydrogen atom donor in the reaction. The trialkylborane/water complex was used for the deoxygenation of xanthates, the dehalogenation of alkyl iodides, and the chemoselective deoxygenation of a xanthate in the presence of alkyl bromides and chlorides. Attempts were made to deliver the hydrogen intramolecularly via a tethered alcohol in order to render the reduction stereoselective. The Securinega alkaloids are a small family of indolizidine and pyrrolizidine natural products. A flexible route utilizing an enantioselective rhodium carbenoid-initiated O-H insertion/Claisen rearrangement/1,2-allyl migration domino sequence was developed targeting the tertiary alcohol moiety common to many members of this family. The strategy was implemented in the synthesis of (+)-norsecurinine and (+)-allonorsecurinine.

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