Journal
NATURE COMMUNICATIONS
Volume 6, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms9617
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Funding
- National Science Foundation of China [21372016, 21472006, 21402002]
- 863 Program [2013AA092903]
- Guangdong Natural Science Foundation [2014A030312004]
- NSFC-Shandong Joint Fund for Marine Science Research Centers [U1406402]
- Shenzhen Basic Research Program [JCYJ20130329180217059, ZDSYS20140509094114168, JSGG20140717102922014]
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The development of an efficient diastereoselective synthesis of the oxabicyclo[3.2.1]octane ring system bearing two oxygenated quaternary chiral centres represents a significant challenge. This motif can be found in a wide range of natural products with significant biological activities. Here we report the synthesis of such kind of scaffold using a cyclohexane-trans-1,4-diol with an alkyne side chain in the presence of Au(I) catalyst. This is a domino process in which two C-H, two C-O and one C-C bond is assembled through a sequence of cyclization/semi-pinacol rearrangements. This strategy has been successfully applied to the asymmetric formal total synthesis of (+)-cortistatins.
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