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Dissertation/Thesis Abstract

Total Synthesis of Polyene Natural Products Lucilactaene and Gymnoconjugatin: Development of a Boron-Tin Linchpin
by Walczak, Matthew C., Ph.D., The Ohio State University, 2008, 221; 10631362
Abstract (Summary)

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.

Indexing (document details)
Advisor: Coleman, Robert S.
Commitee: Coleman, Robert S., Danforth, Douglas L., Forsyth, Craig J., Stambuli, James P.
School: The Ohio State University
Department: Chemistry
School Location: United States -- Ohio
Source: DAI-B 78/11(E), Dissertation Abstracts International
Subjects: Chemistry
Keywords: Cross coupling, Gymnoconjugatin, Lucilactaene, Polyenes, Stille, Total synthesis
Publication Number: 10631362
ISBN: 978-0-355-01614-7
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