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.

Beilstein J. Org. Chem. 2022, 18, 1589–1595. doi:10.3762/bjoc.18.169

Source: Beilstein Journal of Organic Chemistry - November 23, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: benzo[c]phenanthridine alkaloids 1,5-enyne formal total synthesis gold catalysis macarpine Letter Source Type: research