Citation: Zhenhao Wang, Yuliang Tang, Ruyu Li, Shuai Tian, Yu Tang, Dehai Li. Bioinspired synthesis of cochlearol B and ganocin A[J]. Chinese Chemical Letters, ;2024, 35(7): 109247. doi: 10.1016/j.cclet.2023.109247 shu

Bioinspired synthesis of cochlearol B and ganocin A

Zhenhao Wang ^a ,
Yuliang Tang ^a ,
Ruyu Li ^a ,
Shuai Tian ^c ,
Yu Tang ^{a, b, c, *,} ,
Dehai Li ^{a, b, *,}

a.
Key Laboratory of Marine Drugs Chinese Ministry of Education/ Sanya Oceanographic Institute, Ocean University of China, Qingdao 266003/Sanya 572025, China
b.
Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China
c.
Marine Biomedical Research Institute of Qingdao, Ocean University of China, Qingdao 266071, China

tangyu@ouc.edu.cn

dehaili@ouc.edu.cn

Received Date: 10 August 2023
Revised Date: 15 October 2023
Accepted Date: 23 October 2023
Available Online: 30 October 2023

Figures(6)

Described here is a divergent, biosynthetically inspired synthesis of cochlearol B and ganocin A. Key steps of the synthesis include the chromene unit construction through a biomimetic acid-catalyzed [4 + 2] ring cyclization. A photochemical [2 + 2] cycloaddition was featured to construct the cyclobutane core of cochlearol B. Different skeletal rearrangements of cochlearol B afforded ganocin A, that one of them was Lewis acid mediated epoxide rearrangement and another was DDQ induced cyclobutane formed tetrahydrofuran ring. The described syntheses not only achieved these natural products in an efficient manner, but also provided insight into the biosynthetic relationship between the two different skeletons.
- Biomimetic rearrangement,
- Avarane skeleton,
- Cascade reactions,
- Lewis acid,
- Total synthesis
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