Related Experiment Video
Updated: Mar 17, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Biomimetic Total Synthesis of Hyperjapones A-E and Hyperjaponols A and C
Hiu C Lam1, Justin T J Spence1, Jonathan H George2
1Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
Abstract:
Hyperjapones A-E and hyperjaponols A-C are complex natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A-E using a biomimetic, oxidative hetero-Diels-Alder reaction to couple together dearomatized acylphloroglucinol and cyclic terpene natural products. Hyperjapone A is proposed to be the biosynthetic precursor of hyperjaponol C through a sequence of: 1) epoxidation; 2) acid-catalyzed epoxide ring-opening; and 3) a concerted, asynchronous alkene cyclization and 1,2-alkyl shift of a tertiary carbocation. Chemical mimicry of this proposed biosynthetic sequence allowed a concise total synthesis of hyperjaponol C to be completed in which six carbon-carbon bonds, six stereocenters, and three rings were constructed in just four steps.
More Related Videos
07:14Fabrication of a Biomimetic Nano-Matrix with Janus Base Nanotubes and Fibronectin for Stem Cell Adhesion
Published on: May 10, 2020
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Biosynthesis of Lipids
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Biosynthesis of Nucleic Acids
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Biosynthesis in Bacteria