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

TY - JOUR

T1 - Synthesis of macrocyclic and medium-sized ring thiolactones via the ring expansion of lactams

AU - Palate, Kleopas Y

AU - Epton, Ryan G

AU - Whitwood, Adrian C

AU - Lynam, Jason M

AU - Unsworth, William P

PY - 2021/2/14

Y1 - 2021/2/14

N2 - 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.

AB - 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.

U2 - 10.1039/d0ob02502j

DO - 10.1039/d0ob02502j

M3 - Article

C2 - 33491715

SN - 1477-0520

VL - 19

SP - 1404

EP - 1411

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -