Brominative cyclizations of geranyl derivatives

Thomas R. Hoye, Mark J. Kurth

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

Homogeranic acid (1) and methyl geranylacetoacetate (18) were cyclized with bromine in the presence of silver fluoroborate to the brominated bicyclic compounds 2 and 19, respectively. Proton initiated cyclization competed with the brominative cyclization and gave trans lactone 3 and enol ether 20, respectively. Acid-catalyzed cyclization of 1 to 3 and isomerization of 3 to the cis lactone 5 were investigated. Both 3 and 5 were converted to the natural product dihydroactinidiolide (14).

Original languageEnglish (US)
Pages (from-to)3693-3697
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number19
StatePublished - 1978
Externally publishedYes

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Cyclization
Lactones
Derivatives
Bromine
Acids
Isomerization
Biological Products
Silver
Ether
Protons

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hoye, T. R., & Kurth, M. J. (1978). Brominative cyclizations of geranyl derivatives. Journal of Organic Chemistry, 43(19), 3693-3697.

Brominative cyclizations of geranyl derivatives. / Hoye, Thomas R.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 43, No. 19, 1978, p. 3693-3697.

Research output: Contribution to journalArticle

Hoye, TR & Kurth, MJ 1978, 'Brominative cyclizations of geranyl derivatives', Journal of Organic Chemistry, vol. 43, no. 19, pp. 3693-3697.
Hoye, Thomas R. ; Kurth, Mark J. / Brominative cyclizations of geranyl derivatives. In: Journal of Organic Chemistry. 1978 ; Vol. 43, No. 19. pp. 3693-3697.
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