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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-02, Vol.19 (6), p.1404-1411
Hauptverfasser: Palate, Kleopas Y, Epton, Ryan G, Whitwood, Adrian C, Lynam, Jason M, Unsworth, William P
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Sprache:eng
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02502j