Cyclisation vs acylL migration OF α-allyl lactone dreived anion : Synthesis of spiro[4,5]dec-2-ene-1,6-diones

• Main Authors: W. Jaivisuthunza, B. Tarnchompoo, C. Thebtaranonth, Y. Thebtaranonth
• Other Authors: Mahidol University
• Format: Article
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry; Pharmacology, Toxicology and Pharmaceutics
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/17543

Directed by substituent R1, the α-allyl-γ-butyrolactone 9 either undergoes cyclisation to give the alcoholic cyclopentenone 12 or 1,2-acyl migration to give 13, when subjected to treatment with LDA in THF/TMEDA. An effective strategy to nullify this directive influence, and dictate cyclisation, is e...