Bioinspired synthesis of cochlearol B and ganocin A

Zhenhao Wang ¹Yuliang Tang ¹Ruyu Li ¹Shuai Tian ²Yu Tang ³Dehai Li⁴

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作者信息

1. Key Laboratory of Marine Drugs Chinese Ministry of Education/Sanya Oceanographic Institute,Ocean University of China,Qingdao 266003/Sanya 572025,China
2. Marine Biomedical Research Institute of Qingdao,Ocean University of China,Qingdao 266071,China
3. Key Laboratory of Marine Drugs Chinese Ministry of Education/Sanya Oceanographic Institute,Ocean University of China,Qingdao 266003/Sanya 572025,China;Laboratory for Marine Drugs and Bioproducts,Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China;Marine Biomedical Research Institute of Qingdao,Ocean University of China,Qingdao 266071,China
4. Key Laboratory of Marine Drugs Chinese Ministry of Education/Sanya Oceanographic Institute,Ocean University of China,Qingdao 266003/Sanya 572025,China;Laboratory for Marine Drugs and Bioproducts,Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China
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Abstract

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 tetrahy-drofuran 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.

Key words

Biomimetic rearrangement/Avarane skeleton/Cascade reactions/Lewis acid/Total synthesis

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基金项目

National Natural Science Foundation of China(U2006204)

National Natural Science Foundation of China(21772181)

National Natural Science Foundation of China(U1906212)

Taishan Scholar Youth Expert Program in Shandong Province(tsqn201812021)

Marine S&T Fund of Shandong Province for the Pilot National Laboratory for Marine Science and Technology(Qingdao)(2022QNLM030003)

Hainan Provincial Joint Project of Sanya Yazhou Bay Science and Technology City(2021CXLH0012)

出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCDCSCD

影响因子：0.771

ISSN：1001-8417

参考文献量57

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