Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

Abstract

The formal total synthesis of macarpine was accomplished by the construction of a naphthol intermediate in Ishikawa’s synthetic route with two different synthetic routes. The convergent synthetic strategies feature the utilization of Au(I)-catalyzed cycloisomerizations of a 1,5-enyne and alkynyl ketone substrates, which were prepared by Sonogashira coupling reactions.

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

“…Gold(I)-catalyzed arylalkyne annulations provide abundant strategies for the syntheses of benzene derivatives, including the strategies shown in this chapter and several other intramolecular or intermolecular strategies [35][36][37][38][39][40][41][42][43][44][45][46][47]. In 2021, the Hashmi group reported the syntheses of metaand paradihydroxynaph thalenes based on diazoalkynes through a regiodivergent gold-catalyzed cyclization (Scheme 13) [34].…”

“…Gold(I)-catalyzed arylalkyne annulations provide abundant strategies for the syntheses of benzene derivatives, including the strategies shown in this chapter and several other intramolecular or intermolecular strategies [35][36][37][38][39][40][41][42][43][44][45][46][47].…”