Natural products possessing multiple carbon-carbon double bonds, known as polyenes, are widely distributed among plant, animal, bacterial and fungal species. Many of these compounds possess potentially useful biological activity. Polyenes from fungi of the genus Fusarium sp. have been a rich source of biologically active natural products, including the polyene lucilactaene.
In this thesis, the development of a hetero-bis-metalated 1,3-butadiene is described for the use in the linchpin coupling of synthetic fragments of the polyene side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain.
Using this strategy, the total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps. This strategy was also made use of in the synthesis of two polyenylfurans, gymnoconjugatin A and B.
|Advisor:||Coleman, Robert S.|
|Commitee:||Coleman, Robert S., Danforth, Douglas L., Forsyth, Craig J., Stambuli, James P.|
|School:||The Ohio State University|
|School Location:||United States -- Ohio|
|Source:||DAI-B 78/11(E), Dissertation Abstracts International|
|Keywords:||Cross coupling, Gymnoconjugatin, Lucilactaene, Polyenes, Stille, Total synthesis|
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