Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal.

Journal article

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.

Authors: George, J; Baldwin, J; Adlington, R

• Publication status: Published
• Journal: Organic letters
• Volume: 12
• Issue: 10
• Pages: 2394-2397
• Publication date: 2010-05-01
• DOI: 10.1021/ol100756z
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Molecular Conformation; Diterpenes; Stereoisomerism; Terpenes