Citation: Zhiwen Chu, Ruiqi Tong, Yufan Yang, Xuanyi Song, Tian bao Hu, Yu Fan, Chen Zhao, Lu Gao, Zhenlei Song. Diverse synthesis of the C ring fragment of bryostatins via Zn/Cu-promoted conjugate addition of α-hydroxy iodide with enone[J]. Chinese Chemical Letters, ;2021, 32(1): 1-4. doi: 10.1016/j.cclet.2020.11.039 shu

Diverse synthesis of the C ring fragment of bryostatins via Zn/Cu-promoted conjugate addition of α-hydroxy iodide with enone

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

lugao@scu.edu.cn

zhenleisong@scu.edu.cn

Received Date: 19 October 2020
Revised Date: 16 November 2020
Accepted Date: 19 November 2020
Available Online: 1 December 2020

Figures(5)

A convergent approach to 1,5-hydroxy ketones, the general precursors for constructing the C ring of bryostatins, has been developed via a Zn/Cu-promoted conjugate addition of α-hydroxy iodides with enones. The reaction leads to direct formation of the C21-C22 bond and tolerates diverse functionalities at the C17-, C18- and C24-positions. The approach also enables a more concise synthesis of the known C ring intermediate (10 longest linear steps and 14 total steps), in contrast to its previous synthesis (17 longest linear steps and 22 total steps) in our total synthesis of bryostatin 8.
- Bryostatins,
- Zn/Cu-promoted conjugate addition,
- α-Hydroxy iodide,
- Enones,
- 1,5-Hydroxy ketones
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