Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products

TAŞKAYA ASLAN S., Menges N., BALCI M.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.11, pp.897-905, 2015 (SCI-Expanded) identifier identifier

  • 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.