Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

Thomas J Cogswell; Craig S Donald; Rodolfo Marquez

doi:10.3762/bjoc.16.15

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

Beilstein J Org Chem. 2020 Jan 28:16:135-139. doi: 10.3762/bjoc.16.15. eCollection 2020.

Authors

Thomas J Cogswell¹, Craig S Donald², Rodolfo Marquez^{1

3}

Affiliations

¹ School of Chemistry, University of Glasgow, Glasgow, G12 8QQ, U.K.
² Lucideon Limited., Queens Road, Penkhull, Stoke-on-Trent, Staffordshire, ST4 7LQ, U.K.
³ School of Physical and Chemical Sciences, University of Canterbury, Christchurch, 8140, New Zealand.

Abstract

A fast, protecting-group-free synthesis of dihydropyridinones has been developed. Starting from commercially available aldehydes, a novel one-pot amidoallylation gave access to diene compounds in good yields. Ring-closing metathesis conditions were then employed to produce the target dihydropyridinones efficiently and in high yields.

Keywords: amidoallylation; aza-goniothalamin; dihydropyridinones; protecting-group-free; ring-closing metathesis; two-pot procedure.

Grants and funding

We would like to thank the EPSRC and AstraZeneca for postgraduate support (T.C.) and for a Leadership Fellowship (R.M.). The authors also thank Dr. Ian Sword and the EPSRC (grant EP/H005692/1) for funding.