posted on 2024-01-29, 17:15authored byJack Buntine, Samrat Dasgupta, Keely Dorney, Oscar Rubinstein, Mina Salimimarand, Jonathan M. White, Mark A. Rizzacasa
The first total synthesis of myxobacteria metabolite
icumazole
A (1) is reported. Key steps in the route include an
organocatalyzed asymmetric self-aldol reaction followed by an acetate
aldol reaction to form the stereotriad present in the oxazole moiety,
an intramolecular Diels–Alder reaction to form the isochromanone,
and an acetylide addition and selective methylation. The final steps
involved a high-yielding modified Cadiot–Chodkiewicz coupling
and stereoselective reduction to secure the Z,Z-diene
and afford 1.