Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine

Qing Zhang, Fu-Min Zhang (), Chang-Sheng Zhang, Si-Zhan Liu, Jin-Miao Tian, Shao-Hua Wang, Xiao-Ming Zhang and Yong-Qiang Tu ()
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Qing Zhang: Lanzhou University
Fu-Min Zhang: Lanzhou University
Chang-Sheng Zhang: Lanzhou University
Si-Zhan Liu: Lanzhou University
Jin-Miao Tian: Shanghai Jiao Tong University
Shao-Hua Wang: Lanzhou University
Xiao-Ming Zhang: Lanzhou University
Yong-Qiang Tu: Lanzhou University

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: Abstract (‒)-Morphine, which is selected as an essential medicine by World Health Organization, is widely applied in the treatment of the pain-related diseases. Due to its synthetically challenging molecular architecture and important clinical role, extensive synthetic studies of morphine-type alkaloids have been conducted. However, catalytic asymmetric total synthesis of (‒)-morphine remains a long-standing challenge. Here, we disclose an efficient enantioselective total synthesis of (‒)-morphine in a longest linear sequence of 16 steps. The key transformation features a highly enantioselective Robinson annulation enabled by our spiro-pyrrolidine catalyst to rapidly construct the densely functionalized cis-hydrodibenzofuran framework containing vicinal stereocenters with an all-carbon quaternary center. This asymmetric approach provides an alternative strategy for the synthesis of (‒)-morphine and its analogues.

Date: 2019
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DOI: 10.1038/s41467-019-10398-4

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