Journal
TETRAHEDRON
Volume 66, Issue 30, Pages 5671-5674Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.057
Keywords
Bruguierol; Total synthesis; Nature product; Cycloaddition; Cyclopropane
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Funding
- National Natural Science Foundation of China [20972069]
- National Key Project of Scientific and Technical Supporting Programs (973 Program) [2010CB126106]
- Ministry of Education of China [RFDF20070055022]
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Total synthesis of natural product (+/-)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)(3)-catalyzed intramolecular [3+2] cycloaddition of cyclopropane, which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products. (C) 2010 Elsevier Ltd. All rights reserved.
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