Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.11, pp.897-905, 2015 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 11
- Publication Date: 2015
- Doi Number: 10.3762/bjoc.11.101
- Journal Name: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.897-905
- Keywords: alkyne cyclization, gold-catalyzed reaction, indolo-oxazin-1-one, marine natural products, pyrrolo-oxazin-1-one, LAMELLARIN-O, LUKIANOL-A, SELECTIVE SYNTHESIS, ACETYLENIC ACIDS, ALKALOIDS, CYCLIZATION, CYCLOISOMERIZATION, 1,3-DIENES, REACTIVITY, HYDRATION
- Middle East Technical University Affiliated: Yes
Abstract
Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.