Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction

Junkai Fu, Yueqing Gu, Hao Yuan, Tuoping Luo, Song Liu, Yu Lan (), Jianxian Gong () and Zhen Yang ()
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Junkai Fu: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Yueqing Gu: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Hao Yuan: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Tuoping Luo: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS) and Peking-Tsinghua Center for Life Sciences, Peking University
Song Liu: School of Chemistry and Chemical Engineering, Chongqing University
Yu Lan: School of Chemistry and Chemical Engineering, Chongqing University
Jianxian Gong: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Zhen Yang: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: Abstract 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.

Date: 2015
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DOI: 10.1038/ncomms9617

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