Synthesis of macrocyclic and medium-sized ring thiolactones via the ring expansion of lactams

Kleopas Y Palate, Ryan G Epton, Adrian C Whitwood, Jason M Lynam, William P Unsworth

Research output: Contribution to journalArticlepeer-review

Abstract

A side chain insertion method for the ring expansion of lactams into macrocyclic thiolactones is reported, that can also be incorporated into Successive Ring Expansion (SuRE) sequences. The reactions are less thermodynamically favourable than the analogous lactam- and lactone-forming ring expansion processes (with this notion supported by DFT data), but nonetheless, three complementary protecting group strategies have been developed to enable this challenging transformation to be achieved.

Original languageEnglish
Pages (from-to)1404-1411
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number6
Early online date18 Jan 2021
DOIs
Publication statusPublished - 14 Feb 2021

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