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Scalable Synthesis of Cyclocitrinol

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journal contribution
posted on 15.07.2018, 00:00 by Yu Wang, Wei Ju, Hailong Tian, Weisheng Tian, Jinghan Gui
A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.