Access to a Guanacastepene and Cortistatin-Related Skeleton via Ethynyl Lactone Ireland-Claisen Rearrangement and Transannular (4 + 3)-Cycloaddition of an Azatrimethylenemethane Diyl

Oleksandr Zhurakovskyi, Sam R. Ellis, Amber L. Thompson, Jeremy Robertson*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

8 Citations (Scopus)

Abstract

Heating a 2,5-furanocyclic (2-azidoethyl)allene initiates a cascade reaction comprising azide-allene cycloaddition, loss of nitrogen, and azatrimethylenemethane (ATMM) diyl-furan transannular (4 + 3)-cycloaddition. The major product of this reaction contains the pentacyclic core common to guanacastepenes D and H and radianspenes J-L; in addition, the central oxa-bridged cycloheptene ring, flanked by two carbocyclic rings, is structurally related to the ABC-ring system found in the cortistatins. This is the first reported synthetic application of a "free" (nonconjugated) ATMM. The cyclization precursors were prepared via the first reported examples of the Ireland-Claisen rearrangement of an ethynyl lactone.

Original languageEnglish
Pages (from-to)2174-2177
Number of pages4
JournalOrganic Letters
Volume19
Issue number8
DOIs
Publication statusPublished - 21 Apr 2017

Fingerprint Dive into the research topics of 'Access to a Guanacastepene and Cortistatin-Related Skeleton via Ethynyl Lactone Ireland-Claisen Rearrangement and Transannular (4 + 3)-Cycloaddition of an Azatrimethylenemethane Diyl'. Together they form a unique fingerprint.

Cite this