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

Issued Date

1996-04-29

Resource Type

Article

ISSN

00404039

DOI

10.1016/0040-4039(96)00494-7

Other identifier(s)

2-s2.0-0029997292

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.37, No.18 (1996), 3199-3202

Suggested Citation

W. Jaivisuthunza, B. Tarnchompoo, C. Thebtaranonth, Y. Thebtaranonth Cyclisation vs acylL migration OF α-allyl lactone dreived anion : Synthesis of spiro[4,5]dec-2-ene-1,6-diones. Tetrahedron Letters. Vol.37, No.18 (1996), 3199-3202. doi:10.1016/0040-4039(96)00494-7 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/17543

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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

Author(s)

W. Jaivisuthunza
 B. Tarnchompoo
 C. Thebtaranonth
 Y. Thebtaranonth

Other Contributor(s)

Mahidol University
 Thailand National Center for Genetic Engineering and Biotechnology

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.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/17543

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Scopus 1991-2000