Bioinspired synthesis of cochlearol B and ganocin A

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外文摘要：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.

外文关键词：

Biomimetic rearrangementAvarane skeletonCascade reactionsLewis acidTotal synthesis

作者：

Zhenhao Wang、Yuliang Tang、Ruyu Li、Shuai Tian、Yu Tang、Dehai Li

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作者单位：

Key Laboratory of Marine Drugs Chinese Ministry of Education/Sanya Oceanographic Institute,Ocean University of China,Qingdao 266003/Sanya 572025,China

Marine Biomedical Research Institute of Qingdao,Ocean University of China,Qingdao 266071,China

Laboratory for Marine Drugs and Bioproducts,Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China

基金：

National Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaTaishan Scholar Youth Expert Program in Shandong ProvinceMarine S&T Fund of Shandong Province for the Pilot National Laboratory for Marine Science and Technology(Qingdao)Hainan Provincial Joint Project of Sanya Yazhou Bay Science and Technology City

项目编号：

U200620421772181U1906212tsqn2018120212022QNLM0300032021CXLH0012

出版年：

2024

DOI：

10.1016/j.cclet.2023.109247

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(7)