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 cyclizatio...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.展开更多
基金supported by the National Natural Science Foundation of China(Nos.U2006204,21772181,U1906212)Taishan Scholar Youth Expert Program in Shandong Province(No.tsqn201812021)+1 种基金the Marine S&T Fund of Shandong Province for the Pilot National Laboratory for Marine Science and Technology(Qingdao)(No.2022QNLM030003)the Hainan Provincial Joint Project of Sanya Yazhou Bay Science and Technology City(No.2021CXLH0012)。
文摘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.
