An Approach Towards the Total Synthesis of Clonostachydiol

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The syntheses of the unsymmetrical 14-membered bismacrolides have been reviewed. A total synthesis of clonostachydiol, the latest to join this family, has been attempted using trimethylsilyl acetylene as the builiding block and palladium catalyzed reactions for the formation of key bonds. The alkyne groups were introduced by Stille coupling of trimethylstannylethynyltrimethylsilane with an acid chloride for one fragment and by addition of lithiotrimethylsilyl acetylene to an aldehyde for the other. Lactic acid derivatives were chosen as starting materials for both fragments, thus introducing two of the chiral centers. The remaining stereocenters were introduced using stereoselective reductions of ketones.

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vi, 83 leaves : ill.

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Maiti, Tushar B. (Tushar Baran) August 1995.

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  • Maiti, Tushar B. (Tushar Baran)

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The syntheses of the unsymmetrical 14-membered bismacrolides have been reviewed. A total synthesis of clonostachydiol, the latest to join this family, has been attempted using trimethylsilyl acetylene as the builiding block and palladium catalyzed reactions for the formation of key bonds. The alkyne groups were introduced by Stille coupling of trimethylstannylethynyltrimethylsilane with an acid chloride for one fragment and by addition of lithiotrimethylsilyl acetylene to an aldehyde for the other. Lactic acid derivatives were chosen as starting materials for both fragments, thus introducing two of the chiral centers. The remaining stereocenters were introduced using stereoselective reductions of ketones.

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vi, 83 leaves : ill.

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  • August 1995

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  • March 26, 2014, 9:30 a.m.

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  • June 26, 2014, 11:47 a.m.

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Maiti, Tushar B. (Tushar Baran). An Approach Towards the Total Synthesis of Clonostachydiol, thesis, August 1995; Denton, Texas. (digital.library.unt.edu/ark:/67531/metadc278800/: accessed July 15, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .