1417601-02-5Relevant articles and documents
Total synthesis of the lycopodium alkaloid serratezomine a using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin
Pigza, Julie A.,Han, Jeong-Seok,Chandra, Aroop,Mutnick, Daniel,Pink, Maren,Johnston, Jeffrey N.
, p. 822 - 843 (2013/04/10)
Serratezomine A is a member of the structurally diverse class of compounds known as the Lycopodium alkaloids. The key supporting studies and successful total synthesis of serratezomine A are described in this account. Significant features of the synthesis include the first application of free radical mediated vinyl amination and Hwu's oxidative allylation in a total synthesis and an intramolecular lactonization via a transannular SNi reaction. Minimal use of protecting groups and the highly diastereoselective formation of a hindered, quaternary stereocenter using an umpolung allylation are also highlights from a strategy perspective. Observation of quaternary carbon epimerization via a retro-Mannich/Mannich sequence highlights the additional challenge presented by the axial alcohol at C8 in serratezomine A.