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Synfacts 2009(6): 0582-0582  
DOI: 10.1055/s-0029-1216674
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Laurefucin

Contributor(s): Philip Kocienski, Stewart Eccles
B. Kim, M. Lee, M. J. Kim, H. Lee, S. Kim, D. Kim*, M. Koh, S. B. Park, K. J. Shin
Seoul National University and Korea Institute of Science and Technology, Seoul, Korea
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Publikationsdatum:
25. Mai 2009 (online)

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Significance

(-)-Laurefucin was isolated from the red alga Laurencia nipponica. The key step in the synthesis is the construction of the 2,8-dioxabi­cyclo[5.2.1]decane skeleton by a phenylselenyl-induced electrophilic cyclization (B → H) which is probably analogous to the biogenesis.