A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

Abstract

A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C were achieved. The four-step total synthesis comprised mainly a Michael addition, a Weinreb amide-activated substitution and a sequence of ketalation/PtO2-catalysed dearomatisation/reductive amination reactions that resulted in ring closure in 13.7% overall yield. The formal synthesis was accomplished in 29.7% overall yield.

Total synthesis of huperserratines A and B

“…22 In addition, huperserratine A (1) exhibited moderate anti-HIV-1 activity with an EC 50 value of 52.91 µg mL −1 . As part of our continuing interest in developing novel synthetic strategies toward Lycopodium alkaloids, [23][24][25] we herein report the first total synthesis of huperserratines A (1) and B (2) through a 12-step sequence from the known chemical (5R)-2-iodo-5-methyl-2-cyclohexen-1one (9).…”