Total Synthesis of (±)-Phainanoid A

Key words

(±)-phainanoid A - dammarane triterpenoid - radical polyene cyclization - semipinacol rearrangement - intramolecular alkenylation

Significance

Dong and co-workers report the total synthesis of (±)-phainanoid A, a dammarane-type triterpenoid featuring a complex scaffold consisting of ten rings and 13 chiral centers.

Comment

The cyclobutane moiety in J was accessed via Pd-catalyzed intramolecular alkenylation. The five-membered ring in the natural product was achieved with a 1,4-addition, which was followed by homoallylic elimination to form the three-­membered ring.

Publication History

Article published online:
18 January 2022