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Synfacts 2011(8): 0814-0814  
DOI: 10.1055/s-0030-1260754
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Basiliolide B and C8-Epimer and Transtaganolides C and D

Contributor(s): Steven V. Ley, Sean Newton
H. M. Nelson, K. Murakami, S. C. Virgil, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
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Publikationsdatum:
20. Juli 2011 (online)

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Significance

Basiliolide B and transtaganolides C and D were isolated from plants belonging to the genus Thapsia. They consist of four rings including a bridging lactone and a cyclic acyl ketene acetal. This synthetic approach utilizes both geraniol E and geraniol derivative E′ (obtained in four steps) to enable divergent total syntheses of the natural products. These are the first total syntheses of these natural products and of any members of this class.