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Title: Cyclisation vs acylL migration OF α-allyl lactone dreived anion : Synthesis of spiro[4,5]dec-2-ene-1,6-diones
Authors: W. Jaivisuthunza
B. Tarnchompoo
C. Thebtaranonth
Y. Thebtaranonth
Mahidol University
Thailand National Center for Genetic Engineering and Biotechnology
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 29-Apr-1996
Citation: Tetrahedron Letters. Vol.37, No.18 (1996), 3199-3202
Abstract: 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 exemplified in a model synthesis of spiro[4,5]dec-2-ene-1,6-dione 19 by a one-pot tandem cyclisation - elimination process starting from 16. Copyright © 1996 Elsevier Science Ltd.
ISSN: 00404039
Appears in Collections:Scopus 1991-2000

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