Synthesis of the core ring system of the yuzurimine-type Daphniphyllum alkaloids by cascade condensation, cyclization, cycloaddition chemistry
I Coldham, L Watson, H Adams…
文献索引：Burrell, Adam J. M.; Coldham, Iain; Watson, Luke; Oram, Niall; Pilgram, Christopher D.; Martin, Nathaniel G. Journal of Organic Chemistry, 2009 , vol. 74, # 6 p. 2290 - 2300
Addition of hydroxylamine to substituted 4-chlorobutanals gives intermediate nitrones that undergo tandem cyclization and then intramolecular dipolar cycloaddition to give the core ring system of the yuzurimine-type natural products. Ring-opening of the isoxazolidines gives amino alcohols that can be converted to 1, 3-oxazines, representing the tetracyclic core of alkaloids such as daphcalycic acid and daphcalycine.
