Citation: Rui Guo, Hongbin Zhai, Yun Li. Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4, C10-di-epi-trans-fused [5-7]-bicyclic skeleton[J]. Chinese Chemical Letters, ;2021, 32(4): 1400-1402. doi: 10.1016/j.cclet.2020.09.023 shu

Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4, C10-di-epi-trans-fused [5-7]-bicyclic skeleton

Rui Guo ^{a, b} ,
Hongbin Zhai ^{c, *,} ,
Yun Li ^{a, *,}

a.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
b.
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, United States
c.
The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China

zhaihb@pku.edu.cn

liyun@lzu.edu.cn

Received Date: 15 August 2020
Revised Date: 3 September 2020
Accepted Date: 15 September 2020
Available Online: 16 September 2020

Figures(5)

Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5+2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.
- Pseudolaric acid B,
- Enantioselective synthesis,
- Sharpless asymmetric epoxidation,
- Intramolecular [5+2] cycloaddition
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