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

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JournalOrganic & biomolecular chemistry
DateAccepted/In press - 17 Jan 2021
DateE-pub ahead of print - 18 Jan 2021
DatePublished (current) - 14 Feb 2021
Issue number6
Volume19
Number of pages8
Pages (from-to)1404-1411
Early online date18/01/21
Original languageEnglish

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.

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