Journal
NATURE COMMUNICATIONS
Volume 5, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms6707
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Funding
- National Science Foundation of China [21372016, 21402002]
- 863 Program [2013AA092903]
- 973 Program [2010CB833201, 2012CB722602]
- NSFC-Shandong Joint Fund for Marine Science Research Centers [U1406402]
- Shenzhen Basic Research Program [JCYJ20130329180217059, GJHS20120628101219325, ZYC201105170335A, ZYC201105170358A]
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The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (-)-lingzhiol (4) for the first time in 17 steps.
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