First Total Synthesis of (–)-Merrillianin

Abstract

The first total synthesis of (–)-merrillianin (1), which is a natural sesquiterpene with a tri- fused structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereo structure determination of naturally occurring (–)-1.

Total Synthesis of the Sesquiterpene (−)-Merrillianin

“…In conclusion, we successfully demonstrated the asymmetric synthesis of (−)-merrillianin ( 1 ) using tricyclic dilactone 19 as a key intermediate in a total yield of 1.6% from 9 using the longest linear sequence of 30 steps . The synthesis consists of an asymmetric Mukaiyama aldol reaction, SmI 2 -mediated reductive intramolecular coupling, an intramolecular Michael reaction, and Wacker-type oxidation.…”