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Pitt CHEM 2320 - Total Synthesis and Structure Elucidation of Bistramide

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1Total Synthesis & StructureElucidation of BistramideP. Wipf - Chem 2320 - Journal ClubLowe, Jason T.; Wrona, Iwona E.; Panek, James S. Total Synthesis ofBistramide A. Organic Letters ACS ASAP.21. Introduction2. Structure Elucidation3. Panek Group Synthesis4. ConclusionsThis topic was selected to highlight allylic silane chemistryand to introduce modern multi-step natural product targetsynthesis.2Synthetic work:• Wipf, P.; Uto, Y.; Yoshimura, S. Chem. Eur. J. 2002, 8,1670.• Statsuk, A. V.; Liu, D.; Kozmin, S. A. JACS 2004, 126,9546.• Wipf, P.; Hopkins, T. D. Chem. Commun. 2005, 3421.• Crimmins, M. T.; Debaillie, A. C. JACS 2006, 128, 4936.Bistramide binds to ActinRizvi, S. A.; Tereshko, V.; Kossiakoff, A. A.; Kozmin,S. A. J. Am. Chem. Soc. 2006, 128, 3882-3883.The eukaryotic cytoskeleton. Actinfilaments are shown in red, microtubulesin green, and the nuclei are in blue.3Systematic Assignment of the Configuration of FlexibleNatural Products by Spectroscopic & ComputationalMethodsZuber, G.; Goldsmith, M.-R.; Hopkins, T. D.; Beratan, D. N.; Wipf, P., "Systematic Assignment of theConfiguration of Flexible Natural Products by Spectroscopic and Computational Methods: The BistramideC Analysis." Org. Lett. 2005, 7, 5269-5272.4Lowe, Jason T.; Wrona, Iwona E.; Panek, James S. Total Synthesis ofBistramide A. Organic Letters ACS ASAP.567Conclusions:• Synthesis is convergent (3 fragments)• Novelty lies in the preparation of the fragments• 3 Organosilanes are used to construct 8 of 11stereogenic carbons• Segment selection and condensation strategy


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Pitt CHEM 2320 - Total Synthesis and Structure Elucidation of Bistramide

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