172605-68-4Relevant academic research and scientific papers
Total Synthesis of (-)-Daphnezomines A and B
Li, Chao,Li, Luyang,Lu, Yunan,Wu, Jinbao,Xu, Guangpeng
supporting information, p. 15240 - 15245 (2020/10/20)
Daphnezomines A and B are structurally unusual Daphniphyllum alkaloids that contain a unique aza-adamantane core skeleton. Herein, a modular approach to these alkaloids is presented that exploits a diverse array of reaction strategies. Commencing from a chiral pool terpene-(S)-carvone, the azabicyclo[3.3.1]nonane backbone, which occurs widely in Daphniphyllum alkaloids, was easily accessed through a Sharpless allylic amination and a palladium-catalyzed oxidative cyclization. A protecting group enabled a stereoselective B-alkyl Suzuki-Miyaura coupling sequence and an Fe-mediated hydrogen atom transfer (HAT)-based radical cyclization were then applied to construct C6 and C8 stereocenters. A final epimer locking strategy enabled the assembly of the highly congested aza-adamantane core, thereby achieving the first total synthesis of (-)-daphnezomines A and B in 14 steps.
New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers
Magnus, Philip,Lacour, Jerome,Coldham, Iain,Mugrage, Benjamin,Bauta, William B.
, p. 11087 - 11110 (2007/10/02)
Triisopropylsilyl enol ethers react with (TsN)2Se to give α-N-tosylamino derivatives in modest to good yields.In the absence of 1,3-diaxial interactions the N-tosylamino group prefers an axial conformation.The axial N-tosylamino derivatives can be readily transformed into the azabicyclononane skeleton, the core structure of a number of alkaloids.
