Asymmetric Total Synthesis of (2 R)-Hydroxynorneomajucin, a Norsesquiterpene from Illicium jiadifengpi

Org Lett. 2022 May 13;24(18):3411-3415. doi: 10.1021/acs.orglett.2c01207. Epub 2022 May 2.

Abstract

We report the first total synthesis of (2R)-hydroxynorneomajucin, a norsesquiterpene derived from the Illicium genus. This natural product displays neurotrophic properties. Small molecule neurotrophins have potential as therapeutics in neurodegenerative diseases. Key steps of our synthesis include a Tsuji-Trost reaction, a Pauson-Khand cyclization, and a Nagata hydrocyanation. A simple sequence of reductions and a Mukaiyama hydration introduce the A-ring substituents with the correct configurations. The overall synthesis was completed in 17 steps (longest linear sequence, LLS).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products*
  • Cyclization
  • Illicium*
  • Stereoisomerism

Substances

  • Biological Products