ol100756z_si_001.pdf (439.66 kB)

Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal

Download (439.66 kB)
journal contribution
posted on 21.05.2010 by Jonathan H. George, Jack E. Baldwin, Robert M. Adlington
A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction.