Densely functionalised spirocyclic oxetane-piperidine scaffolds for drug discovery. Issue 4 (15th February 2018)

• Record Type: Journal Article
• Authors: Geary, Gemma C.; Nortcliffe, Andrew; Pearce, Christopher A.; Hamza, Daniel; Jones, Geraint; Moody, Christopher J.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 4(2018)
• Page Start: 791
• Page End: 797
• Publication Date: 2018-02-15
• Subjects: Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2017.12.012
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Gold catalysed rearrangement of a propargylic alcohol leads to densely finctionaised spirocyclic oxetane-piperidine scaffolds for drug discovery. Abstract: A spirocyclic, sp 3 -atom rich oxetane-containing scaffold was synthesised in just two steps via a gold catalysed propargylic alcohol rearrangement. The key gold cyclisation can be undertaken on a 40 g scale allowing the preparation of 419 lead-like compounds based on the scaffold for the European Lead Factory.